The Five-membered Hetero Ring Is One Of The Cyclos In A Bicyclo Ring System Patents (Class 544/143)
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Patent number: 4874761Abstract: 4-Arylcarbonyl-1-[(4-morpholinyl)-lower-alkyl]-1H-indoles, useful as analgesic agents, are prepared by reaction of a 3-arylcarbonyl-2-methylnitrobenzene with DMF dimethyl acetal; reductive cyclization of the product with hydrogen over a catalyst; and N-alkylation of the resulting 4-arylcarbonylindole with an appropriate 4-(halo-lower-alkyl)morpholine in the presence of a strong base.Type: GrantFiled: April 12, 1989Date of Patent: October 17, 1989Assignee: Sterling Drug Inc.Inventors: Thomas E. D'Ambra, Malcolm R. Bell
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Patent number: 4855448Abstract: 2-Amino-3-aroyl-.gamma.-oxobenzenebutanoic acids and derivatives having the formula: ##STR1## wherein X is hydrogen, halogen, or loweralkyl; Y is hydrogen, halogen, loweralkyl, loweralkoxy, nitro, or trifluoromethyl; n is 1 or 2; and R is hydrogen, loweralkyl, or a pharmaceutically acceptable cation, are disclosed having anti-inflammatory activity.Type: GrantFiled: August 8, 1988Date of Patent: August 8, 1989Assignee: A. H. Robins Company, IncorporatedInventor: David A. Walsh
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Patent number: 4853408Abstract: Novel 4-phenylpropyl-indoles of the formula ##STR1## wherein R and R.sub.1 are individually selected from the group consisting of hydrogen, linear alkyl of 1 to 5 carbon atoms, branched alkyl of 3 to 5 carbon atoms, cycloalkyl of 3 to 7 carbon atoms cycloalkylalkyl of 4 to 7 carbon atoms and optionally substituted aralkyl of 7 to 12 carbon atoms or R.sub.1 and R taken together with the nitrogen atom form an optionally unsaturated heterocycle containing another heteroatom selected from the group consisting of oxygen, sulfur and nitrogen optionally substituted with a member of the group consisting of alkyl of 1 to 5 carbon atoms, phenyl, naphthyl and aralkyl of 7 to 12 carbon atoms, a together with b forms .dbd.0 or a together with c form a carbon-carbon bond, b is hydrogen or with a forms .dbd.0, c is hydrogen or with a forms a carbon-carbon bond, the dotted line is an optional carbon-carbon bond, A is --(CH.sub.2).sub.n --, is an integer from 2 to 5, R.sub.Type: GrantFiled: April 17, 1986Date of Patent: August 1, 1989Assignee: Roussel UclafInventors: Francois Clemence, Jacques Guillaume, Gilles Hamon
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Patent number: 4851406Abstract: The present invention provides indole derivatives of the general formula: ##STR1## wherein R.sub.1 is a hydrogen atom or an alkyl, alkenyl, cycloalkyl, cycloalkenyl, carboxyl, cyano, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or aryl radical, R.sub.2 is a hydrogen atom or an alkyl, trihalogenomethyl, hydroxyl, cycloalkyl, cyano, carboxyl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl radical; R.sub.2 is a heterocyclic five-membered ring containing 1 to 4 heteroatoms or a heterocyclic six-membered ring containing 1 to 5 heteroatoms, the heteroatoms of the five- and six-membered rings being the same or different and being nitrogen, oxygen or sulphur and one or more of the nitrogen atoms optionally carrying an oxygen atom, the said five- and six-membered rings optionally being substituted by one or more alkyl, alkoxy, alkylthio, oxo, hydroxyl, nitro, amino, halogen or cyano groups; or R.sub.Type: GrantFiled: September 4, 1986Date of Patent: July 25, 1989Assignee: Boehringer Mannheim GmbHInventors: Alfred Mertens, Wolfgang von der Saal, Walter-Gunar Friebe, Bernd Muller-Beckmann, Gisbert Sponer
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Patent number: 4840950Abstract: 4-Arylcarbonyl-1-[(4-morpholinyl)-lower-alkyl]-1H-indoles, useful as analgesic agents, are prepared by reaction of a 3-arylcarbonyl-2-methylnitrobenzene with DMF dimethyl acetal; reductive cyclization of the product with hydrogen over a catalyst; and N-alkylation of the resulting 4-arylcarbonylindole with an appropriate 4-(halo-lower-alkyl)morpholine in the presence of a strong base.Type: GrantFiled: February 11, 1987Date of Patent: June 20, 1989Assignee: Sterling Drug Inc.Inventors: Thomas E. D'Ambra, Malcolm R. Bell
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Patent number: 4840963Abstract: Novel 2-sulfamoyl-1H-indoles and derivatives thereof are shown to be useful for the treatment of elevated intraocular pressure in pharmaceutical compositions designed for systemic or topical ophthalmic administration.Type: GrantFiled: December 7, 1984Date of Patent: June 20, 1989Assignee: Merck & Co., Inc.Inventors: Kenneth L. Shepard, Samuel L. Graham
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Patent number: 4837235Abstract: This invention provides a series of novel keto sulfones of formula I ##STR1## in which the group .dbd.A-- is selected from .dbd.C(Ra)-- and .dbd.N-- and the other radicals have the meanings defined in the following specification.The compounds of formula I are leukotriene antagonists. The invention also provides pharmaceutically acceptable salts of the formula I compounds; pharmaceutical compositions containing the formula I compound, or their salts, for use in the treatment of, for example, allergic or inflammatory diseases, or endotoxic or traumatic shock conditions; and processes for the manufacture of the formula I compounds, as well as intermediates for use in such manufacture.Type: GrantFiled: October 16, 1986Date of Patent: June 6, 1989Assignee: ICI Americas Inc.Inventors: Peter R. Bernstein, Frederick J. Brown, Victor G. Matassa, Ying K. Yee
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Patent number: 4826974Abstract: Pyrrolo[1,2-a]azepinone derivatives of formula: ##STR1## in which R.sub.3 is H or halogen and either (A) R is benzyl or phenylthio in which the phenyls are optionally substituted by one or more halogens or hydroxy, alkyl, alkyloxy or alkylthio radicals, R.sub.1 and R.sub.2, which may be identical or different, denote alkyl optionally substituted by dialkylamino in which the alkyls are optionally joined to form a 1-pyrrolidinyl, piperidino, morpholino or 1-piperazinyl ring substituted by alkyl, or alternatively R.sub.1 and R.sub.2 form a heterocyclic ring chosen from pyrrolidine, piperidine, morpholine and piperazine, substituted by alkyl, alkenyl (2 to 4 C), benzyl or phenethyl optionally substituted by halogen, alkyl, alkyloxy, alkylthio, CF.sub.Type: GrantFiled: November 4, 1987Date of Patent: May 2, 1989Assignee: Rhone-Poulenc SanteInventors: Michel Barreau, Marie-Therese Comte, Daniel Farge, Jean-Luc Malleron, Gerard Ponsinet, Gerard Roussel
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Patent number: 4818757Abstract: Compounds of the formula ##STR1## are disclosed. These compounds are useful as hypotensive agents due to their angiotensin converting enzyme inhibition activity and depending upon the definition of X may also be useful as analgesics due to their enkephalinase inhibition activity.Type: GrantFiled: December 28, 1987Date of Patent: April 4, 1989Assignee: E. R. Squibb & Sons, Inc.Inventors: Harold N. Weller, III, Eric M. Gordon
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Patent number: 4808609Abstract: A compound selected from the group consisting of hydroxyalkoxy-4-phenylpropyl-indoles of the formula ##STR1## wherein R and R.sub.1 are individually selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, cycloalkylalkyl of 4 to 7 carbon atoms and aralkyl of 7 to 12 carbon atoms optionally substituted with 1 to 3 members of the group consisting of halogen, methyl, ethyl, methoxy, ethoxy, --CF.sub.3, --NO.sub.2, CH.sub.3 S-- and --NH.sub.2 or R.sub.1 and R together with the nitrogen atom to which they are attached form an optionally unsaturated heterocycle optionally containing --S--, --O-- or ##STR2## R' is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, phenyl, naphthyl and phenylalkyl of 7 to 12 carbon atoms, a and b form =O and c is hydrogen or a and c form a carbon-carbon bond and b is hydrogen, the dotted line is an optional double bond, A is ##STR3## m is 1,2 or 3, R.sub.Type: GrantFiled: June 25, 1986Date of Patent: February 28, 1989Assignee: Roussel UclafInventors: Francois Clemence, Jacques Guillaume, Gilles Hamon
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Patent number: 4798892Abstract: The present invention relates to compounds of the general formula ##STR1## wherein Ar represents a substituted or unsubstituted heterocyclic group; W represents alkylene of from 1 to about 10 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1, NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1, wherein R.sub.1, R.sub.2 and R.sub.3 may be alike or different and may be hydrogen, alkyl, alkoxyalkyl cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1, or R.sub.1 and R.sub.3 may together with N form a 5 to 7 membered heterocyclic group and the pharmaceutically acceptable salts thereof. The compounds exhibit beta-adrenergic blocking activity and are also useful in the treatment of glaucoma.Type: GrantFiled: April 14, 1986Date of Patent: January 17, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventors: Sheung T. Kam, William L. Matier, Ghanshyam Patil, Khuong H. X. Mai
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Patent number: 4791109Abstract: Novel indole-carboxamides of the formula ##STR1## wherein R and R.sub.1 are individually selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, cycloalkylalkyl of 4 to 7 carbon atoms and aralkyl of 7 to 12 carbon atoms optionally substituted with 1 to 3 members of the group consisting of halogen, methyl, ethyl, methoxy, ethoxy, --CF.sub.3, CH.sub.3 S--, --NH.sub.2 and --NO.sub.2 or R.sub.1 and R taken together with the nitrogen atom form an optionally unsaturated heterocycle optionally containing a member of the group consisting of --O--, --S-- and ##STR2## R' is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, phenyl, naphthyl, aralkyl of 7 to 12 carbon atoms and substituted phenyl, R.sub.3 is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, alkoxy of 1 to 3 carbon atoms, chlorine, bromine, iodine, --NO.sub.2, --NH.sub.Type: GrantFiled: July 10, 1986Date of Patent: December 13, 1988Assignee: Roussel UclafInventors: Francois Clemence, Jacques Guillaume, Gilles Hamon
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Patent number: 4785016Abstract: Indole derivatives are disclosed of formula (I): ##STR1## wherein R.sub.1 represents H, alkyl or alkenyl;R.sub.2 represents H, alkyl, alkenyl, cycloalkyl or phenyl or phenyl alkyl the phenyl ring being optionally substituted by halogen, alkyl, alkoxy, hydroxyl or by a group --NR.sub.a R.sub.b, or --CONR.sub.a R.sub.b, wherein R.sub.a and R.sub.b are H, alkyl, alkenyl, or with the nitrogen atom form a saturated monocyclic ring;R.sub.3 and R.sub.4 are H, alkyl or propenyl or together form an aralkylidene group;Alk represents a Cf.sub.2-3 alkyl chain optionally substituted by one or two alkyl groups; andA.sup.1 represents a C.sub.2-5 alkenyl chain and salts and solvates thereof.The compounds have selective vasoconstrictor activity and are useful in treating and/or preventing pain resulting from dilatation of the cranial vasculature, particularly migraine. The compounds may be formulated in conventional manner with pharmaceutically acceptable carriers or excipients.Type: GrantFiled: December 3, 1985Date of Patent: November 15, 1988Assignee: Glaxo Group LimitedInventors: Brian Evans, Alexander W. Oxford, Darko Butain
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Patent number: 4777168Abstract: A class of bicyclic benzo-oxy heterocyclic ether and thioether compounds exhibiting parmacological activity, including anti-secretory and anti-ulcerogenic activity, pharaceutical compositions comprising these compounds, and methods for the treatment of gastrointestinal hyperacidity and ulcerogenic disorders in mammals using said compositions.Type: GrantFiled: January 7, 1988Date of Patent: October 11, 1988Assignee: Rorer Pharmaceutical CorporationInventors: Donald E. Kuhla, Henry F. Campbell, William L. Studt, Kent W. Neuenschwander
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Patent number: 4774240Abstract: The invention relates to N-indolylethyl-sulphonic acid amides of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are defined in the specification and X is carboxyl, alkoxycarbonyl, cyano or carboxamido. These active compounds are useful in medicaments in combating thromboses, thromboembolisms, allergies or asthmatic disorders.Type: GrantFiled: April 14, 1986Date of Patent: September 27, 1988Assignee: Bayer AktiengesellschaftInventors: Horst Boshagen, Ulrich Rosentreter, Folker Lieb, Hermann Oediger, Friedel Seuter, Elisabeth Perzborn, Volker-Bernd Fiedler
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Patent number: 4739106Abstract: A process for preparing a 2-carbamoyloxyalkyl-1,4-dihydropyridine derivative represented by the general formula: ##STR1## which comprises: (a) reacting a 3-amino-3-carbamoyloxyalkylacrylic acid derivative represented by the general formula: ##STR2## with a benzylidene compound represented by the general formula: ##STR3## (b) reacting the 3-amino-3-carbamoyloxyalkylacrylic acid derivative of the general formula II with an aldehyde compound represented by the general formula: ##STR4## and a .beta.-keto-ester compound represented by the general formula:R.sup.4 --CO--CH.sub.2 --COOR.sup.2 (V)(c) reacting a 3-carbamoyloxyalkylpropiolic acid derivative represented by the general formula: ##STR5## with the benzylidene compound of the general formula III and ammonia or its salt; or(d) reacting the 3-carbamoyloyalkylpropiolic acid derivative of the general formula VI with the aldehyde compound of the general formula IV, the .beta.-keto-ester compound of the general formula V and ammonia or its salt.Type: GrantFiled: May 16, 1986Date of Patent: April 19, 1988Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Tetsuji Miyano, Kunio Suzuki, Nobuo Harada
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Patent number: 4735957Abstract: New thiazole derivatives of the formula: ##STR1## wherein R.sup.1 is lower alkyl, carboxy, a drivative of carboxy, hydroxymethyl, halomethyl, lower alkylthiomethyl, hydroxyiminomethyl or alkenyl which may be substituted with lower alkoxycarbonyl, pyridyl or cyano,R.sup.2 is hydrogen, hydroxy, lower alkyl, pyridyl, amino, lower alkylamino, pyridylamino, arylamino, acylamino, N-(lower)alkylN-acylamino, guanidino optionally substituted with dimethylaminomethylene, or ar(lower)alkylamino optionally substituted with lower alkoxy,R.sup.3 is lower alkyl, halo(lower)alkyl or N-containing unsaturated heterocyclic group which may be substituted with halogen, lower alkyl, lower alkoxy, carboxy, a derivative of carboxy, hydroxy, pyridyl, amino, lower alkylamino, pyridylamino, arylamino, acylamino, N-(lower)alkyl-N-acylamino, guanidino, N-oxide or ar(lower)alkylamino optionally substituted with lower alkoxy,Q is --CO--, andn is an integer of 0 or 1,provided that when both of R.sup.1 and R.sup.Type: GrantFiled: November 18, 1986Date of Patent: April 5, 1988Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Hisashi Takasugi
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Patent number: 4705857Abstract: Indole derivatives of formula I ##STR1## R is hydrogen, one or two halogen atoms or one or two organic radicals in the 4-, 5-, 6- or 7-position(s),R.sup.1 and R.sup.4 are the same or different and each is hydrogen, alkyl of 1 to 3 carbon atoms or alkoxyalkyl of 1 to 3 carbon atoms in each of the alkoxy and alkyl portions,R.sup.3 is phenyl, --COOalkyl, --PO.sub.3 (alkyl).sub.2, --SO.sub.2 aryl, --SO.sub.2 alkyl, ##STR2## each of 1 to 3 carbon atoms in each alkyl group, and A and B each independently is alkyl of 1 to 3 carbon atoms or together with the connecting N-atom form a pyrrolidono, piperidino, morpholino or piperazino group,are valuable intermediates for preparing valuable tryptophans and .beta.-carbolines.Type: GrantFiled: October 28, 1983Date of Patent: November 10, 1987Assignee: Schering AktiengesellschaftInventor: Helmut Biere
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Patent number: 4699907Abstract: Novel racemic mixtures and optical isomers of 4-morpholinyl-1H-indoles of the formula: ##STR1## wherein R and R.sub.1 are individually selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and R.sub.2 is selected from the group consisting of hydroxymethyl, alkylthiomethyl of 1 to 3 alkyl carbons, cyanomethyl and carboxy optionally esterified with an aliphatic alcohol of 1 to 5 carbon atoms or optionally amidified with an amine of the formula ##STR2## R.sub.3 is alkyl of 1 to 4 carbon atoms and R.sub.4 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having the ability to activate neurons and to protect the same against ischemic or anoxic aggressions.Type: GrantFiled: December 12, 1986Date of Patent: October 13, 1987Assignee: Roussel UclafInventors: Jean-Claude Gasc, Lucien Nedelec, Claude Rettien, Dinah W. Nanopoulos
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Patent number: 4650811Abstract: Novel ethenylphenol indoles of the formula ##STR1## wherein R and R.sub.1 are individually selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, cycloalkylalkyl of 4 to 7 carbon atoms and aralkyl of 7 to 12 carbon atoms optionally substituted with 1 to 3 members of the group consisting of halogen, methyl, ethyl, methoxy, ethoxy, methylthio, --CF.sub.3, --NH.sub.2 and --NO.sub.2 or R and R.sub.1 together with the nitrogen atom form an optionally unsaturated heterocycle optionally containing a second heteroatom selected from the group consisting of --O--, --S-- and ##STR2## R' is hydrogen or alkyl of 1 to 5 carbon atoms, a together with X is .dbd.0 and b is hydrogen or a together with b is a carbon-carbon bond and X is hydrogen, the dotted line indicates the possibility of a double bond with the compounds having the trans configuration if a double bond, A is selected from the group consisting of ##STR3## and --(CH.sub.2).sub.n --, n is 2,3,4 or 5, R.Type: GrantFiled: January 14, 1985Date of Patent: March 17, 1987Assignee: Roussel UclafInventors: Jacques Guillaume, Francois Clemence, Neil L. Brown
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Patent number: 4603202Abstract: Fluorans of the formula (I) ##STR1## where R.sup.1 is hydrogen or methyl, R.sup.2 is hydrogen or unsubstituted or substituted alkyl, R.sup.3 is hydrogen, unsubstituted or substituted alkyl, cycloalkyl or unsubstituted or substituted phenyl, or ##STR2## is a 5-membered or 6-membered saturated heterocyclic radical, R.sup.4 and R.sup.5 independently of one another are each hydrogen, alkyl, alkoxy or halogen, R.sup.6 is hydrogen, halogen, alkyl, alkoxy, phenylalkoxy, phenoxy, phenyl or unsubstituted or substituted amino, or is pyrrolidinyl, piperidinyl or morpholinyl, R.sup.7 is hydrogen, alkyl or halogen, R.sup.8 is C.sub.1 -C.sub.5 -alkyl, and the radicals R.sup.4 and R.sup.5 and/or R.sup.6 and R.sup.7 together may furthermore each be a --CH.dbd.CH--CH.dbd.CH-- bridge, and the fused-on benzo ring may be further substituted, are used for the preparation of pressure-sensitive and heat-sensitive recording materials.Type: GrantFiled: October 12, 1984Date of Patent: July 29, 1986Assignee: BASF AktiengesellschaftInventors: Udo Mayer, Andreas Oberlinner
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Patent number: 4600776Abstract: Cationic enamine dyestuffs of the general formula ##STR1## in which the symbols have the meaning given in the description, are used for dyeing natural and synthetic substrates and compositions which can be dyed with cationic dyestuffs, in particular paper.Type: GrantFiled: June 11, 1984Date of Patent: July 15, 1986Assignee: Bayer AktiengesellschaftInventors: Karlheinrich Meisel, Roderich Raue
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Patent number: 4581354Abstract: 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: July 15, 1985Date of Patent: April 8, 1986Assignee: Sterling Drug Inc.Inventor: Malcolm R. Bell
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Patent number: 4562201Abstract: The present invention relates to new compounds of the formula ##STR1## where X is ##STR2## 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 aryl. These compounds are useful in the treatment of various cardiac arrhythmias.Type: GrantFiled: July 26, 1982Date of Patent: December 31, 1985Assignee: American Hospital Supply CorporationInventors: David M. Stout, William L. Matier
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Patent number: 4542148Abstract: Oxindole derivatives of the general formula I ##STR1## are described, and also processes for their preparation and drugs containing them. The new compounds exhibit a neuroanabolic action in various animal models.Type: GrantFiled: April 7, 1982Date of Patent: September 17, 1985Assignee: Hoechst AktiengesellschaftInventors: Heinz Kuch, Hansjorg Kruse
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Patent number: 4507483Abstract: 3-[(Substituted-amino)(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 amines or precursors thereof in the presence of a base.Type: GrantFiled: March 9, 1983Date of Patent: March 26, 1985Assignee: The Hilton-Davis Chemical Co.Inventors: Paul J. Schmidt, William M. Hung
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Patent number: 4495352Abstract: 1-Aryloxy-3-[(3-indolyl)-tert.-butyl]amino-2-propanols having a heterocyclic aryl-attached substituent or aryl-fused heterocyclic ring are antihypertensive agents having vasodilator and adrenergic .beta.-receptor blocking action.Type: GrantFiled: December 3, 1981Date of Patent: January 22, 1985Assignee: Mead Johnson & CompanyInventors: William E. Kreighbaum, William T. Comer
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Patent number: 4398030Abstract: 3-[(Substituted-amino)(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 amines or precursors thereof in the presence of a base.Type: GrantFiled: January 22, 1982Date of Patent: August 9, 1983Assignee: Sterling Drug Inc.Inventors: Paul J. Schmidt, William M. Hung
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Patent number: 4382934Abstract: A compound of the general formula: ##STR1## wherein R.sup.1 and R.sup.2 are hydrogen, halogen, lower alkyl, lower alkoxy, halo (lower) alkyl, lower alkanoylamino, lower alkoxyalylamino, or a 5 to 6 membered saturated or unsaturated heterocyclic group having at least one imino group, and selected from the group consisting of pyrrolidinyl, pyrrolinyl, imidazolidinyl, piperazinyl, piperidyl, and morpholynyl,or R.sup.1 and R.sup.2 are combined together to form a benzene ring,R.sup.3 is oxo or a group of the formula .dbd.N--OR.sup.5, in which R.sup.5 is hydrogen or lower alkyl,R.sup.4 is mono- or di- or triphenyl (lower) alkyl,A is C.sub.1 to C.sub.7 alkylene and its hydroxy derivatives,Y is (C.sub.1 to C.sub.3) alkylene,or a pharmaceutically acceptable salt thereof.Said compounds having antiallergic properties represent inclusively all of the possible optical and/or geometrical isomers due to the asymmetric carbon and carbon-nitrogen double bond.Type: GrantFiled: October 10, 1979Date of Patent: May 10, 1983Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Tsutomu Teraji, Teruo Oku, Takayuki Namiki
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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: 4353833Abstract: Compounds of the general formula I ##STR1## where the radicals A, A.sup.1 and B are identical or different andA is unsubstituted or substituted benzene or heteroaromatic,A.sup.1, if n=1, is unsubstituted or substituted heteroaromatic or is aryl which is unsubstituted or substituted by alkyl, aryl, cycloalkyl, chlorine, bromine, hydroxyl, alkoxy, aryloxy, nitro, hydroxycarbonyl, alkoxycarbonyl, or aminocarbonyl, and, if n>1, A.sup.1 may also be aryl substituted by unsubstituted or substituted amino,B is a bridge member of the formula ##STR2## B.sup.1 is a bridge member which may or may not be quaternized, R.sup.1 and R.sup.2 are hydrogen, unsubstituted or substituted alkyl, cycloalkyl, aryl, alkoxy or amino,n is an integer equal to or greater than 1 andX.sup..theta. is an anion.The compounds according to the invention are preferably used for coloring paper pulp.Type: GrantFiled: November 12, 1980Date of Patent: October 12, 1982Assignee: BASF AktiengesellschaftInventors: Horst Bruder, Hans-Juergen Degen, Franz Feichtmayr, Klaus Grychtol, Udo Mayer
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Patent number: 4333932Abstract: 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.Type: GrantFiled: February 20, 1980Date of Patent: June 8, 1982Assignee: Pfizer Inc.Inventor: John L. Belletire
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Patent number: 4314943Abstract: 1-Aryloxy-3-[(3-indolyl)-tert.-butyl]amino-2-propanols having a heterocyclic aryl-attached substituent or aryl-fused heterocyclic ring are antihypertensive agents having vasodilator and adrenergic .beta.-receptor blocking action.Type: GrantFiled: February 13, 1979Date of Patent: February 9, 1982Assignee: Mead Johnson & CompanyInventors: William E. Kreighbaum, William T. Comer
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Patent number: 4272298Abstract: A process for conditioning a pigment or disperse dye which comprises treating the colorant with liquid ammonia and results in an improvement of the dyeing properties and may be accompanied by a conversion into another modification. The pigments afforded by the instant process are particularly suitable for pigmenting material of high molecular weight.Type: GrantFiled: September 18, 1979Date of Patent: June 9, 1981Assignee: Ciba-Geigy CorporationInventor: Fridolin Babler
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Patent number: 4272533Abstract: 2-aminoethyl-1-phenylindolines are useful as anti-diabetic and anti-obesity agents.Type: GrantFiled: August 27, 1979Date of Patent: June 9, 1981Assignee: Sandoz Ltd.Inventors: Fulvio Gadient, Rudolf Suess
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Patent number: 4264619Abstract: New .alpha.-(cyclic tert. aminophenyl)-aliphatic acids, e.g. those of the formula ##STR1## and functional derivatives thereof, are anti-inflammatory agents.Type: GrantFiled: November 21, 1978Date of Patent: April 28, 1981Assignee: Ciba-Geigy CorporationInventors: Richard W. J. Carney, George deStevens
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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: 4233312Abstract: Novel indoles of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, halogen, --CF.sub.3, alkyl of 1 to 8 carbon atoms and alkoxy of 1 to 8 carbon atoms, R.sub.2 is in the 2, 3 or 4 position and is selected from the group consisting of halogen, --CF.sub.3 and alkyl, alkoxy and alkylthio of 1 to 8 carbon atoms, A is selected from the group consisting of branched alkylene of 3 to 5 carbon atoms and --(CH.sub.2).sub.n -- and n is a number of 2 to 5 and R.sub.3 and R.sub.4 are alkyl of 1 to 8 carbon atoms or taken together with the nitrogen atom form a heterocyclic ring selected from the group consisting of piperidinyl, pyrrolidinyl, morpholinyl, piperazinyl and N-alkyl piperazinyl with 1 to 4 alkyl carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having analgesic activity and their preparation.Type: GrantFiled: May 9, 1978Date of Patent: November 11, 1980Assignee: Roussel UclafInventors: Andre Allais, Jean Meier, Roger Deraedt
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Patent number: 4220763Abstract: 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: August 2, 1979Date of Patent: September 2, 1980Assignee: Sterling Drug Inc.Inventors: Malcolm R. Bell, Rudolf Oesterlin
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Patent number: 4220650Abstract: 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.Type: GrantFiled: October 18, 1978Date of Patent: September 2, 1980Assignee: Pfizer Inc.Inventor: John L. Belletire
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Patent number: 4211706Abstract: The present invention relates to certain structural and pharmacological analogs of cis-17,18-didehydroprostacyclin (PGI.sub.3) wherein a nitrogen atom is substituted for 6,9.alpha.-epoxy-oxygen of prostacyclin. These novel nitrogen containing prostacyclin-type compounds are useful for the same pharmacological purposes for which prostacyclin is used, especially as antithrombotic agents.Type: GrantFiled: October 13, 1978Date of Patent: July 8, 1980Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4210591Abstract: An indolinospiropyrane compound of the formula ##STR1## wherein R.sub.1 represents alkyl which has at most 12 carbon atoms and is unsubstituted or substituted by halogen, hydroxyl, cyano, lower alkoxy or lower alkyl-carbonyloxy, or cycloalkyl, phenyl or benzyl or phenyl or benzyl which are substituted by halogen, nitro, lower alkyl or lower alkoxy,R.sub.2 represents hydrogen, alkyl which has at most 12 carbon atoms and is unsubstituted or substituted by halogen, hydroxyl, cyano, lower alkoxy or lower alkyl-carbonyloxy, or cycloalkyl or benzyl which is unsubstituted or substituted by halogen, nitro, lower alkyl or lower alkoxy, orR.sub.1 and R.sub.Type: GrantFiled: January 21, 1977Date of Patent: July 1, 1980Assignee: Ciba-Geigy CorporationInventor: Peter Burri
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Patent number: 4167632Abstract: Isoindole derivatives of the formula ##STR1## wherein A, Z, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8 and n are as hereinafter set forth, as well as intermediates, are described. The end products of formula I are useful as appetite-suppressants.Type: GrantFiled: July 26, 1978Date of Patent: September 11, 1979Assignee: Hoffmann-La Roche Inc.Inventor: Roland Jaunin
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Patent number: 4161584Abstract: This invention relates to certain structural and pharmacological analogs of prostacyclin (PGI.sub.2) wherein a nitrogen atom is substituted for the 6,9.alpha.-epoxy-oxygen of prostacyclin. These novel nitrogen-containing prostacyclin-type compounds are useful for the pharmacological purposes for which prostacyclin is used, e.g., as antithrombotic agents, antihypertensive agents, antiasthma agents, nasal decongestants, or regulators of fertility and procreation.Type: GrantFiled: April 5, 1978Date of Patent: July 17, 1979Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4160862Abstract: 1-Acyl-3-(amino-lower-alkyl)indoles, useful as anti-inflammatory agents, are prepared either by acylation of a 3-(amino-lower-alkyl)indole; by Fisher indole synthesis from an N'-acylphenylhydrazine and an amino-lower-alkanone; by alkylation of an amine with a 1-acyl-3-(halo-lower-alkyl)indole; or by reductive alkylation of a 1-acyl-3-indole-lower-alkylcarboxaldehyde.Type: GrantFiled: February 4, 1974Date of Patent: July 10, 1979Assignee: Sterling Drug Inc.Inventor: Bernard L. Zenitz
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Patent number: 4153789Abstract: The present invention is concerned with novel 2-unsubstituted-3-phenylindolines acid addition salts thereof. These compounds have been found to have valuable pharmacological properties indicative of possible utility, inter alia, of controlling coagulation of the blood and as hypoglycemic agents. The invention also provides novel processes for producing the novel compounds and pharmaceutical compositions containing same as active ingredients.Type: GrantFiled: March 20, 1978Date of Patent: May 8, 1979Assignee: Delmar Chemicals LimitedInventors: Rudolf Kubela, Vaclav Musil, Lise A. Hughes
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Patent number: 4153609Abstract: A 3-indolyl-3-bis-aminophenyl-phthalide compound of the formula ##STR1## wherein R.sub.1 represents alkyl which has at most 12 carbon atoms and is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, cycloalkyl, or unsubstituted or substituted phenyl or benzyl wherein the substituents are halogen, nitro, lower alkyl or lower alkoxy,R.sub.2 represents hydrogen, alkyl which has at most 12 carbon atoms and is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, cycloalkyl, or benzyl which is unsubstituted or substituted by halogen, nitro, lower alkyl or lower alkoxy, orR.sub.1 and R.sub.2 together with the nitrogen atom linking them represent a 5- or 6-membered heterocyclic radical,X.sub.1 and X.sub.2 independently of one another represent hydrogen, lower alkyl, cycloalkyl, benzyl which is unsubstituted or substituted by halogen, nitro, lower alkyl or lower alkoxy, or acyl having 1 to 8 carbon atoms, and X.sub.Type: GrantFiled: January 10, 1977Date of Patent: May 8, 1979Assignee: Ciba-Geigy CorporationInventors: Jean C. Petitpierre, Robert Garner
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Patent number: 4148895Abstract: The present invention relates to basically substituted indole derivatives and to a process for their manufacture.The novel compounds are valuable medicaments which exhibit hypotensive and antiarrhythmic activity on the cardiac circulation system.Type: GrantFiled: December 16, 1976Date of Patent: April 10, 1979Assignee: Hoechst AktiengesellschaftInventors: Rudolf Lattrell, Wilhelm Bartmann, Joachim Kaiser
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Patent number: 4140854Abstract: 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: October 4, 1977Date of Patent: February 20, 1979Assignee: Sterling Drug Inc.Inventors: Malcolm R. Bell, Rudolf Oesterlin
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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