Plural Isoquinoline Ring Systems Attached Directly Or Indirectly To Each Other By Nonionic Bonding Patents (Class 546/140)
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Patent number: 5240939Abstract: Muscle relaxant nitrogen bridge tetrahydroisoquinolines are disclosed. The novel compounds are represented by the formula ##STR1## wherein A is ##STR2## M represents --(CH.sub.2).sub.n --Z--(CH.sub.2).sub.n or ##STR3## R is a C.sub.1-3 alkoxy group, or adjacent Rs are a methylenedioxy group, R.sub.1 is lower alkyl; n is 1-6;m is 2 or 3; p is 1-3; Z is --N.sup.+ (R.sub.2 R.sub.3)--, --N(R.sub.4)--, ##STR4## and --N[(CH.sub.2).sub.n --A--R.sub.5 ]--; R.sub.2 and R.sub.3 are independently lower alkyl groups wherein a carbon atom within the chain may be replaced by a heteroatom, lower cycloalkyl, lower cycloalkyl lower alkyl, aryl, aryl lower alkyl, a 4- to 6-member heteroring or may be combined with the nitrogen to form a heteroring; R.sub.4 is a straight- or branched- chain C.sub.1-10 alkyl wherein a carbon atom within the chain may be replaced by a heteroatom, lower cycloalkyl, lower cycloalkyl lower alkyl, aryl, or a heteroring, which groups may be substituted or unsubstituted; or ##STR5## R.sub.Type: GrantFiled: November 16, 1992Date of Patent: August 31, 1993Assignee: Anaquest, Inc.Inventor: Donald M. Demko
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Patent number: 5216150Abstract: Novel quinoline sulfonamino derivatives having a vessel smooth muscle relaxation activity as well as a platelet agglutination inhibitory activity and inhibitory activity to protein kinase A, myosin light chain kinase, proteinkinase C, and calmodulindependent proteinkinase II, but having little action or cardio function; a process for the production of the derivatives, and a pharmaceutical composition containing the derivative.Type: GrantFiled: September 12, 1991Date of Patent: June 1, 1993Assignees: Hiroyoshi Hidaka, Tobishi Yakuhin Kogyo Kabushiki KaishaInventors: Hiroyoshi Hidaka, Tomohiko Ishikawa, Masatoshi Hagiwara, Tsutomu Inoue, Kenji Naitoh, Osamu Sakuma, Masayuki Yuasa, Tadashi Morita, Tadashi Toshioka, Isao Umezawa, Takashi Inaba
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Patent number: 5192791Abstract: A novel class of pyrrolidin-2-one and piperidin-2-one compounds in which the nitrogen atom is bonded to an oxyphenyl radical having tertiary-alkyl and tri-methylsilyl substituents. The compounds possess anti-inflammatory, immunomodulatory, analgesic and anti-pyretic activity and they may be combined with excipients to provide formulations which are useful in treating arthritis and conditions associated with that disease.Type: GrantFiled: August 14, 1990Date of Patent: March 9, 1993Assignee: Biofor, Ltd.Inventor: Sung J. Lee
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Patent number: 5162362Abstract: What are disclosed are aminoacid compounds of the formula ##STR1## wherein n is 0 or 1, and salts thereof, said compounds and salts having hypotensive properties; methods for making the compounds; pharmaceutical compositions containing the compounds or salts; and use of the compounds and salts for treating hypertension.Type: GrantFiled: December 27, 1983Date of Patent: November 10, 1992Assignee: Hoechst AktiengesellschaftInventors: Rolf Geiger, Volker Teetz, Hansjorg Urbach, Bernward Scholkens, Rainer Henning
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Patent number: 5142060Abstract: Herbicidal substituted sulphonylaminotriazolinones of the formula ##STR1## in which R.sup.1 represents an optionally substituted radical from the group consisting of alkyl, aralkyl, aryl and heteroaryl,R.sup.2 represents hydrogen or the group --SO.sub.2 --R.sup.1 where R.sup.1 has the abovementioned meaning,R.sup.3 represents hydrogen, halogen, hydroxyl, mercapto, amino or an optionally substituted radical from the group consisting of alkyl, cycloalkyl, aralkyl, aryl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkenylthio, alkinylthio, aralkoxy, aralkylthio, alkylamino and dialkylamino,R.sup.4 represents hydrogen, halogen, hydroxyl, amino or an optionally substituted radical from the group consisting of alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino and dialkylamino,X represents nitrogen or a CH group,Y represents nitrogen or a CR.sup.5 group whereR.sup.Type: GrantFiled: October 17, 1991Date of Patent: August 25, 1992Assignee: Bayer AktiengesellschaftInventors: Klaus-Helmut Muller, Rolf Kirsten, Joachim Kluth, Klaus Konig, Hans-Jochem Riebel, Peter Babczinski, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
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Patent number: 5109002Abstract: There are provided cycloalkyl piperidine compounds which are useful in the treatment of physiological or drug-induced psychosis or dyskinesia in a mammal. These novel compounds are selective sigma receptor antagonists and have a low potential for movement disorder side effects associated with typical antipsychotic agents.Type: GrantFiled: August 20, 1990Date of Patent: April 28, 1992Assignee: Du Pont Merck Pharmaceutical CompanyInventors: Gary A. Cain, Paul J. Gilligan, Sang W. Tam
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Patent number: 5081246Abstract: Novel quinoline sulfonamino derivatives having a vessel smooth muscle relaxation activity as well as a platelet agglutination inhibitory activity and inhibitory activity to protein kinase A, myosin light chain kinase, proteinkinase C, and calmodulindependent proteinkinase II, but having little action or cardio function; a process for the production of the derivatives, and a pharmaceutical composition containing the derivative.Type: GrantFiled: December 20, 1989Date of Patent: January 14, 1992Assignees: Hiroyoshi Hidaka, Tobishi Yakuhin Kogyo Kabushiki KaishaInventors: Horoyoshi Hidaka, Tomohiko Ishikawa, Masatoshi Hagiwara, Tsutomu Inoue, Kenji Naitoh, Osamu Sakuma, Masayuki Yuasa, Tadashi Morita, Tadashi Toshioka, Isao Umezawa, Takashi Inaba
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Patent number: 5071860Abstract: Insecticidally active substituted heteroaryl phenyl ethers of the formula ##STR1## in which Het represents an optionally substituted heteroaromatic radical,X represents O, S, --CH.sub.2 --, --O--CH.sub.2 --, --S--CH.sub.2 --, --CH.sub.2 --O--, ##STR2## Y represents O, --O--CH.sub.2 -- or S, Z represents an optionally substituted aromatic or heteroaromatic radical;m represents integers from 1-4n represents 0, 1, 2, 3, 4O represents 0, 1, 2, 3, 4, provided than n and o do not simultaneously represent 0p represents integers from 1-4,R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently of one another represent hydrogen, C.sub.1 -C.sub.6 -alkyl which is optionally substituted; two radicals adjacent to one another can also, together with the C atoms to which they are bonded, form a saturated carbocyclic 5- or 6-ring,R.sup.1 represents identical or different radicals hydrogen, halogen, CN, C.sub.1-4 -alkyl, 1-5-halogeno-C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylthio, 1-5-halogeno-C.sub.Type: GrantFiled: March 7, 1990Date of Patent: December 10, 1991Assignee: Bayer AktiengesellschaftInventors: Bernd Alig, Wilhelm Stendel, Michael Londershausen
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Patent number: 5070096Abstract: New phenylsulphonamide of the formula in which ##STR1## R.sup.1 represents a pyridyl, quinolyl or isoquinolyl radical which is unsubstituted or substituted by halogen, alkyl, cycloalkyl, alkoxy, cyano, nitro, halogenoalkyl, halogenoalkoxy, alkoxycarbonyl or alkylsulphonyl,R.sup.2 represents hydrogen, cyano, nitro, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy or alkoxycarbonyl,R.sup.3 represents an aryl radical which is unsubstituted or monosubstituted, disubstituted or trisubstituted by halogen, halogenoalkyl, halogenoalkoxy, alkyl, alkoxy, alkylthio, alkylsulphonyl, cyano, nitro or alkoxycarbonyl, the substituents being identical or different, or represents pentafluorophenyl or represents a straight-chain, branched or cyclic alkyl which is unsubstituted or substituted by halogen, aryl, aryloxy, cyano, alkoxycarbonyl, alkoxy, alkylthio or trifluoromethyl, andX represents an --O--, --A--B-- or --B--A-- groupwhereA denotes --O--, ##STR2## and B denotes --CH.sub.2 -- or ##STR3## where R.sup.Type: GrantFiled: November 15, 1990Date of Patent: December 3, 1991Assignee: Bayer AktiengesellschaftInventors: Klaus Mohrs, Elisabeth Perzborn, Friedel Seuter, Romanis Fruchtmann, Christian Kohlsdorfer
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Patent number: 5032590Abstract: Substituted hydroxylamines of the formula ##STR1## in which R.sup.1 stands for an aromatic or heterocyclic radical,are especially useful in the treatment of hyperlipoproteinaemia, lipoproteinaemia and atherosclerosis.Type: GrantFiled: March 8, 1990Date of Patent: July 16, 1991Assignee: Bayer AktiengesellschaftInventors: Walter Hubsch, Rolf Angerbauer, Peter Fey, Hilmar Bischoff, Dieter Petzinna, Delf Schmidt
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Patent number: 4975438Abstract: Compounds of the formula ##STR1## Y is O or S, *A is paraphenylene or *--(CH.sub.2).sub.n --(X).sub.m --(CH.sub.2).sub.r --, X is O, S or --CH.dbd.CH--, n or r, independently, are integers from 0 to 3, s is an integer from 0 to 1, m is an integer from 0 to 1, provided that when m is 1, n+s must be at least 2, R.sub.1 and R.sub.2, independently, are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, Het, Aryl, R.sub.3, R.sub.4 and R.sub.8, independently, are hydrogen, lower alkyl, aryl, R.sub.5 and R.sub.6, independently, are hydrogen or lower alkyl, R.sub.7 is hydrogen, lower alkyl, cycloalkyl, Het-lower alkyl or aryl, Het is a monocyclic 5- or 6-membered hetero aromatic or a bicyclic heteroaromatic radical containing one or two hetero atoms selected from nitrogen, oxygen and sulfur, which radical may be substituted by lower alkyl, halogen or aryl, and the asterisk denotes the point of attachment,and when R.sub.6 and R.sub.7 are different, their enantiomers and racemic mixtures thereof, when R.sub.1 and R.sub.Type: GrantFiled: September 6, 1988Date of Patent: December 4, 1990Assignee: Hoffmann-La Roche Inc.Inventors: Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
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Patent number: 4968681Abstract: Substituted hydroxylamines of the formula ##STR1## in which R.sup.1 stands for an aromatic or heterocyclic radical, are especially useful in the treatment of hyperlipoproteinaemia, lipoproteinaemia and atherosclerosis.Type: GrantFiled: November 15, 1988Date of Patent: November 6, 1990Assignee: Bayer AktiengesellschaftInventors: Walter Hubsch, Rolf Angerbauer, Peter Fey, Hilmar Bischoff, Dieter Petzinna, Delf Schmidt
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Patent number: 4960890Abstract: Methine dyes (I) which conform in one of their tautomeric forms to the general formula ##STR1## where Y.sup.1 is in both or either case an electron-attracting group and the other Y.sup.1 is hydrogen,Y.sup.2 is in each case, independently of the others, hydrogen, --CN, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, phenyl, pyridyl or together with a further Y.sup.2 a five- or six-membered ring which may have a fused-on benzene ring,R is hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.7 -C.sub.10 -aralkyl or .beta.Type: GrantFiled: October 5, 1989Date of Patent: October 2, 1990Assignee: BASF AktiengesellschaftInventors: Ewald Daltrozzo, Werner Sulger
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Patent number: 4937255Abstract: For inhibiting 3-hydroxy-3-methylglutaryl coenzyme A and cholesterol biosynthesis, the novel disubstituted pyrroles of the formula ##STR1## in which R.sup.1 is aryl or heteroaryl,R.sup.2 is cycloalkyl or optionally substituted alkyl,R.sup.3 is hydrogen or cycloalkyl, or optionally substituted alkyl, aryl or heteroaryl,X is --CH.sub.2 --CH.sub.2 -- or --CH.dbd.CH--,A is ##STR2## R.sup.6 is hydrogen or alkyl, and R.sup.7 is hydrogen, a cation or alkyl, aryl or aralkyl.Type: GrantFiled: March 16, 1989Date of Patent: June 26, 1990Assignee: Bayer AktiengesellschaftInventors: Walter Hubsch, Rolf Angerbauer, Peter Fey, Hilmar Bischoff, Dieter Petzinna, Delf Schmidt, Gunter Thomas
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Patent number: 4885299Abstract: The invention relates to new 2-(2,3-dihydro-2-oxo-3-benzofuranyl)acetic acid compounds of general formula I: ##STR1## in which: R.sub.1 denotes a hydrogen atom, a linear or branched alkyl radical having 1 to 4 carbon atoms or a phenyl radical optionally substituted with a halogen atom or with an alkoxy radical containing 1 to 4 carbon atoms or an alkyl radical having 1 to 4 carbon atoms,R.sub.2 denotes a hydrogen or halogen atom, a hydroxyl radical, an alkyl radical having 1 to 4 carbon atoms or an alkoxy radical containing 1 to 4 carbon atoms,R denotes a hydroxyl radical, a linear or branched alkoxy radical having 1 to 4 carbon atoms, a benzyloxy radical or a radical of general formula A: ##STR2## in which: X and Y, which may be identical or different, each denote a linear or branched alkyl radical containing 1 to 5 carbon atoms, a radical of general formula A.sub.Type: GrantFiled: January 17, 1989Date of Patent: December 5, 1989Assignee: ADIR Et CieInventors: Gilbert Lavielle, Jean Lepagnol
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Patent number: 4777286Abstract: Process and compounds for producing intermediates for the production of renin inhibitors.Type: GrantFiled: June 18, 1985Date of Patent: October 11, 1988Assignee: The Upjohn CompanyInventor: Heinrich J. Schostarez
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Patent number: 4761418Abstract: Neuromuscular blocking agents of formula (1) which are useful as skeletal muscle relaxants during surgery are disclosed. ##STR1## and X is an anion, preferably pharmaceutically acceptable.Type: GrantFiled: July 17, 1985Date of Patent: August 2, 1988Assignees: Burroughs Wellcome Co., General Hospital CorporationInventors: Roy A. Swaringen, Jr., Hassan A. El-Sayad, David A. Yeowell, John J. Savarese
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Patent number: 4761473Abstract: Novel compositions are prepared from (1) nitrogen-containing aromatic heterocyclic compound having at least one group of either (a) a carboxylic acid, (b) carboxylic acid ester, (c) carboxylic acid anhydride, (d) carboxylic acid halide, (e) or combination thereof, such as 2-pyridinecarboxylic acid, and (2) an organic fatty amine such as a mixture of C.sub.10 to C.sub.21 fatty amines. These novel compositions are useful as oil and gas well corrosion inhibitors.Type: GrantFiled: October 15, 1985Date of Patent: August 2, 1988Assignee: The Dow Chemical CompanyInventors: Duane S. Treybig, Robert G. Martinez
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Patent number: 4751309Abstract: Methine dyes (I) which conform in one of their tautomeric forms to the general formula ##STR1## where Y.sup.1 is in both or either case an electron-attracting group and the other Y.sup.1 is hydrogen,Y.sup.2 is in each case, independently of the others, hydrogen, --CN, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, phenyl, pyridyl or together with a further Y.sup.2 a five- or six-membered ring which may have a fused-on benzene ring,R is hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.7 -C.sub.10 -aralkyl or .beta.Type: GrantFiled: September 15, 1986Date of Patent: June 14, 1988Assignee: BASF AktiengesellschaftInventors: Ewald Daltrozzo, Werner Sulger
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Patent number: 4749698Abstract: Compounds having the general structure ##STR1## and their pharmaceutically acceptable salts, wherein the substituents are defined herein, which exhibit antihypertensive activity.Type: GrantFiled: July 8, 1985Date of Patent: June 7, 1988Assignee: Rorer Pharmaceutical CorporationInventors: Edward S. Neiss, John T. Suh, John R. Regan, Jerry W. Skiles, Jeffrey N. Barton, James J. Mencel, Paul Menard
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Patent number: 4725605Abstract: This invention relates to a method of treating ulcers or hypersecretion in a mammal which comprises administering a compound of formula ##STR1## or a pharmaceutically acceptable salt thereof wherein --B--B.sup.1 -- represents a chain of formula--CR.sup.5 .dbd.CR.sup.6 -- (Ib)or--(CHR.sup.5).sub.n --CR.sup.6 .dbd. (Ic);R represents an optionally substituted aryl or heteroaryl radical; R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently represent hydrogen, or a defined substituent or any adjacent pair of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 together with the carbon atoms to which they are attached complete a five or six membered saturated or unsaturated carbocyclic or heterocyclic ring, said ring being optionally substituted by a defined substituent said heterocyclic ring having at least one heteroatom selected from oxygen, nitrogen and sulphur. Novel compositions and compounds of formula I are also disclosed.Type: GrantFiled: May 22, 1986Date of Patent: February 16, 1988Assignee: John Wyeth & Brother LimitedInventors: Roger Crossley, Peter J. Meade
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Patent number: 4701460Abstract: Long duration muscle relaxant compound of formula (I) ##STR1## and its use in producing muscle relaxation in mammals including man.Type: GrantFiled: January 25, 1985Date of Patent: October 20, 1987Assignee: Burroughs Wellcome Co.Inventors: Hassan A. El-Sayad, Roy A. Swaringen, Jr., David A. Yeowell
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Patent number: 4698352Abstract: This invention relates to a novel 4-oxo-1,4-dihydronicotinic acid derivative ##STR1## or a salt thereof, wherein R.sup.1 is hydrogen or carboxyl-protecting group;R.sup.2 is substituted phenyl and naphthyl, or a substituted or unsubstituted heterocyclic group; andR.sup.3 is haloalkyl, aminoalkyl, or substituted or unsubstituted alkenyl, phenylalkenyl, naphthylalkenyl, phenylalkyl, naphthylalkyl, phenylalkynyl, naphthylalkynyl, heterocyclic alkyl, heterocyclic alkenyl, phenyl, naphthyl, cycloalkyl, cycloalkenyl, carboxylic acyl, iminoalkyl, heterocyclic or bridged hydrocarbon, which has a broad antibacterial spectrum and a low toxicity, and are useful for treatment of diseases of human beings and animals, to a process for producing the same and to an antibacterial agent containing the same.Type: GrantFiled: October 27, 1983Date of Patent: October 6, 1987Assignee: Toyama Chemical Co., Ltd.Inventors: Hirokazu Narita, Yoshinori Konishi, Jun Nitta, Shunjiro Misumi, Hideyoshi Nagaki, Isao Kitayama, Yoriko Nagai, Yasuo Watanabe, Nobuyuki Matsubara, Shinzaburo Minami, Isamu Saikawa
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Patent number: 4656278Abstract: Isoquinoline derivatives of the formula (I) ##STR1## in which R is a group selected from t-butyl and groups of the formula ##STR2## and R' is selected from methyl and ethyl, are useful in the preparation of 1(2H)-isoquinolone.Type: GrantFiled: May 14, 1985Date of Patent: April 7, 1987Assignee: SynthelaboInventors: Guy Rossey, Didier Legroux
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Patent number: 4656290Abstract: A process is disclosed for the preparation of compounds of the Formula IR--X--R.sup.1 (I)wherein X is thio, dithio or carbonyl and R and R.sup.1 are defined hereinbelow which comprises reducing a compound of the Formula IIR--A (II)wherein A is chlorosulfonyl or a group of the Formula ##STR1## with a sulfur compound comprising sulfur which is of the (+)4 oxidation degree and is converted into the (+)6 oxidation degree during the process or with a sulfur compound which is decomposed in acidic medium to a compound of the latter oxidation degree in the presence of a catalytic amount but not more than 0.5 mole--related to 1 mole of the starting material of the Formula II--of elemental iodine or a compound capable of delivering hydrogen iodide in acidic medium or a compound which can be reduced to hydrogen iodide in acidic medium with the sulfur compound used.Type: GrantFiled: January 16, 1985Date of Patent: April 7, 1987Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.Inventors: Istvan Kaldor, Andras Szasz, Ilona Vegh nee Ba, Jozsef Heizer, Eva Behedek nee Haraszin
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Patent number: 4634716Abstract: Compounds of the formula: ##STR1## where R.sup.3 is ##STR2## where n is 1-3 and the R.sup.a 's and R.sup.b 's are independently hydrogen or loweralkyl; and pharmaceutically acceptable salts thereof; are inhibitors or angiotensin I converting enzyme useful as antihypertensive agents.Type: GrantFiled: May 16, 1983Date of Patent: January 6, 1987Assignee: Merck & Co., Inc.Inventors: William H. Parsons, David Taub
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Patent number: 4595675Abstract: What are disclosed are indole, quinoline and isoquinoline compounds of the formula ##STR1## in which n denotes 0 or 1, m denotes 1 or 2, but (n+m).ltoreq.2, A together with the bridgehead carbon atoms denotes a benzene or a cyclohexane ring, Y.sub.1 denotes hydrogen, lower alkanoyl or lower cycloalkanoyl, benzoyl nicotinoyl or a radical of the formula II, and Y.sub.2 denotes methyl, amino, lower alkanoylamino, lower cycloalkanoylamino, benzoylamino or nicotinoylamino, and salts thereof, useful as hypotensive agents, and methods for making the same.Type: GrantFiled: January 2, 1985Date of Patent: June 17, 1986Assignee: Hoechst AktiengesellschaftInventors: Rolf Geiger, Volker Teetz, Bernward Scholkens, Hans Wissmann
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Patent number: 4501605Abstract: Novel herbicidal thiadiazoles of the formula: ##STR1## (wherein: R.sup.1 represents a group R.sup.a, --S(O)nR.sup.a or --SO.sub.2 NR.sup.a R.sup.b, where R.sup.a and R.sup.b, which may be the same or different, each represent hydrogen, cycloalkyl of 3 to 7 carbon atoms, alkenyl or alkynyl of 2 to 6 carbon atoms, phenyl, phenylalkyl of 7 to 10 carbon atoms, or alkyl of 1 to 10 carbon atoms, any phenyl or alkyl group present being optionally substituted by one or more halogen atoms, cyano groups, alkoxy or alkylthio groups of 1 to 4 carbon atoms, or phenoxy groups, or R.sup.a and R.sup.b together form an alkylene chain of 2 to 6 carbon atoms, and n represents 0, 1 or 2;X represents oxygen or sulphur;Z represents a group --NR.sup.c R.sup.d ; andY represents a group --NR.sup.e R.sup.f or a group --N.dbd.CR.sup.e R.sup.f ; where R.sup.c, R.sup.d, R.sup.e and R.sup.f, which may be the same or different, each represent a group as defined for R.sup.Type: GrantFiled: February 2, 1983Date of Patent: February 26, 1985Assignee: FBC LimitedInventors: Thomas L. Hough, Graham P. Jones
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Patent number: 4491665Abstract: This invention provides the neuromuscular blocking agents of formula (I): ##STR1## where B and C are each a group of formula (II) and are meta or para to one another: ##STR2## wherein D is CH.sub.2 CH.sub.2 or CH.dbd.CH (preferably trans); Y is alkyl of 1-4 carbon atoms (methyl, ethyl, propyl or butyl); E and F and H or OCH.sub.3 ; X.sup.- is an anion, preferably pharmaceutically acceptable; and the substituted benzyl and substituted propyl groups are in a trans relationship relative to each other in the nitrogen-containing ring.Methods for preparing the compounds, pharmaceutical formulations containing the compounds, and their use are also described.Type: GrantFiled: April 13, 1981Date of Patent: January 1, 1985Assignee: Burroughs Wellcome Co.Inventors: Hassan A. El-Sayad, Roy A. Swaringen, Jr., David A. Yeowell
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Patent number: 4414220Abstract: 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: March 1, 1982Date of Patent: November 8, 1983Assignee: Pfizer Inc.Inventor: John L. Belletire
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Patent number: 4408043Abstract: Fluorinated compounds of the formula ##STR1## are disclosed. The cationic amine compounds are useful as surfactants.Type: GrantFiled: March 8, 1982Date of Patent: October 4, 1983Assignee: Nalco Chemical CompanyInventors: Virgil L. Seale, James R. Stanford, James E. Briscoe, Glenn S. Penny
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Patent number: 4404377Abstract: Heterocyclic/aromatic fluorinated compounds of the formula ##STR1## are disclosed. The cationic compounds are useful as surfactants.Type: GrantFiled: March 8, 1982Date of Patent: September 13, 1983Assignee: Nalco Chemical CompanyInventors: Virgil L. Seale, James R. Stanford, James E. Briscoe, Glenn S. Penny
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Patent number: 4385047Abstract: Imidodisulfamide derivatives useful in the treatment of allergic conditions are prepared by reaction of an appropriately substituted tetrahydroisoquinoline and bis-(chlorosulfonyl)imide in the presence of a non-nucleophilic organic base. Pharmaceutical compositions and methods of alleviating the symptoms of an allergic response are also disclosed.Type: GrantFiled: January 5, 1981Date of Patent: May 24, 1983Assignee: SmithKline Beckman CorporationInventor: Fadia E. Ali
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Patent number: 4370332Abstract: A 1,2,3,4-tetrahydroisoquinoline having smooth muscle relaxant activity of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are each hydrogen or lower alkyl, R.sub.3 is phenyl having substituents selected from the group consisting of lower alkenyloxy, mercapto, lower alkylthio, sulfamoyl and mono or disubstituted sulfamoyl, or a heterocyclic group, R.sub.4 and R.sub.5 are each hydroxy or protected hydroxy and X is --O-- or--S--.Type: GrantFiled: October 29, 1980Date of Patent: January 25, 1983Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Teiji Kishimoto, Hiromu Kochi, Yoshiyuki Kaneda
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Patent number: 4369322Abstract: The known synthesis for the production of aromatic substituted acetonitriles by reaction of aromatic substances with cyanogen chloride in the gas phase is improved by feeding the starting materials in gaseous form and separated from each other into the reactor. The process can be used to synthesize in general aromatic and especially hetero-aromatic substituted acetonitrile.Type: GrantFiled: March 9, 1981Date of Patent: January 18, 1983Assignee: Degussa AGInventors: Peter Schalke, Axel Kleemann
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Patent number: 4350698Abstract: Imidosulfamide derivatives useful in the treatment of allergic conditions are prepared by reaction of an appropriately substituted tetrahydroisoquinoline and chlorosulfonylisocyanate in the presence of a non-nucleophilic organic base. Pharmaceutical compositions and methods of inhibiting the symptoms of an allergic response are also disclosed.Type: GrantFiled: September 25, 1981Date of Patent: September 21, 1982Assignee: SmithKline CorporationInventors: John G. Gleason, David T. Hill
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Patent number: 4321254Abstract: Imidodisulfamide derivatives useful in the treatment of allergic conditions are prepared by reaction of an appropriately substituted tetrahydroisoquinoline and bis(chlorosulfonyl)imide in the presence of a tertiary amine. Pharmaceutical compositions and methods of inhibiting the symptoms of an allergic response are also disclosed.Type: GrantFiled: September 26, 1980Date of Patent: March 23, 1982Assignee: SmithKline CorporationInventor: Fadia E. Ali
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Patent number: 4317826Abstract: Imidodisulfamide derivatives useful in the treatment of allergic conditions are prepared by reaction of an appropriately substituted tetrahydroisoquinoline and bis (chlorosulfonyl)imide in the presence of a tertiary amine. Pharmaceutical compositions and methods of inhibiting the symptoms of an allergic response are also disclosed.Type: GrantFiled: May 27, 1980Date of Patent: March 2, 1982Assignee: SmithKline CorporationInventor: John G. Gleason
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Patent number: 4315935Abstract: Imidodisulfamide derivatives useful in the treatment of allergic conditions are prepared by reaction of an appropriately substituted tetrahydroisoquinoline and bis(chlorosulfonyl)imide in the presence of a tertiary amine.Type: GrantFiled: June 13, 1980Date of Patent: February 16, 1982Assignee: SmithKline CorporationInventor: Fadia E. Ali
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Patent number: 4292320Abstract: A 1,2,3,4-tetrahydroisoquinoline having smooth muscle relaxant activity of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are each hydrogen or lower alkyl and X is --O-- or --S--, and pharmaceutically acceptable salts thereof.Type: GrantFiled: August 17, 1979Date of Patent: September 29, 1981Assignee: Fujisawa Pharmaceutical Company, LimitedInventors: Teiji Kishimoto, Hiromu Kochi, Yoshiyuki Kaneda
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Patent number: 4287197Abstract: Isoquinoline derivatives of the formula: ##STR1## wherein R.sub.1 represents alkyl of 1 through 8 carbon atoms, and n represents 1 or 2, are new compounds possessing useful pharmacological properties. They are particularly valuable as analgesic, anti-inflammatory, antipyretic or antiviral agents.Type: GrantFiled: May 6, 1980Date of Patent: September 1, 1981Assignee: Rhone-Poulenc IndustriesInventors: Daniel Farge, Alain Jossin, Gerard Ponsinet, Daniel Reisdorf
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Patent number: 4271296Abstract: Useful intermediates for preparing a 1-dethia-1-oxacephalosporin and represented by the following formula: ##STR1## (wherein R is a monovalent group resulting from the elimination of the carbonyl function of an acyl group derived from a carboxylic or carbonic acid;COB is carboxy or protected carboxy; andX is hydrogen or a nucleophilic group)are prepared from the corresponding penicillin 1-oxides of the following formula: ##STR2## (wherein R, COB, and X are as defined above) by heating, if required in the presence of a desulfurizing reagent, or by exchanging the X group with another one under the condition of an appropriate nucleophilic substitution.Type: GrantFiled: January 14, 1980Date of Patent: June 2, 1981Assignee: Shionogi & Co., Ltd.Inventors: Teruji Tsuji, Mitsuru Yoshioka, Shoichiro Uyeo, Yoshio Hamashima, Ikuo Kikkawa, Wataru Nagata
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Patent number: 4242346Abstract: Bis-2N-alkylene tetrahydroisoquinoline compounds are inhibitors of phenylethanolamine N-methyl-transferase.Type: GrantFiled: December 19, 1979Date of Patent: December 30, 1980Assignee: SmithKline CorporationInventor: Robert M. DeMarinis
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Patent number: 4235906Abstract: Intermediate-duration reversible neuromuscular blocking agents of the formula (I) ##STR1## where B and C are preferably para or may be meta and are each ##STR2## where W is CH.sub.2 or most preferably CH.dbd.CH R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are the same or different and are each hydrogen or lower alkoxy of 1 to 4 carbon atoms and preferably methoxy, Y is lower alkyl of 1 to 4 carbon atoms and preferably methyl, Z is hydrogen, lower alkyl of 1 to 4 carbon atoms, cyclopentyl, cyclohexyl, benzyl, or ##STR3## where ALKYL has 1 to 4 carbon atoms preferably where the O-ALKYL is at the 2, 3, 4 or 5 positions such as 4-methoxy benzyl and is most preferably 3,4-dimethoxy benzyl or 3, 4, 5-trimethoxybenzyl, n is 2, 3 or 4, most preferably 2 or 3 provided that at least one of R.sub.1 to R.sub.4 is lower alkoxy and most preferably where R.sub.1 and R.sub.4 is hydrogen and R.sub.2 and R.sub.3 are methoxy and X is a pharmaceutically acceptable anion.Type: GrantFiled: January 31, 1979Date of Patent: November 25, 1980Assignee: Massachusetts General HospitalInventors: John J. Savarese, Richard J. Kitz, Sara Ginsburg
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Patent number: 4192877Abstract: Short acting reversible neuromuscular blocking agents of the formula (I) ##STR1## where B and C is preferably meta or maybe para ##STR2## where m is 2, 3 or 4 and is preferably 2,R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are the same or different and are hydrogen or lower alkoxy of 1 to 4 carbon atomsY is lower alkyl of 1 to 4 carbon atomsn is 2, 3 or 4, most preferably 3, provided that at least one of R.sub.1 to R.sub.4 and one of R.sub.5 to R.sub.7 is lower alkoxy and X is a pharmaceutically acceptable anion. These neuromuscular blocking agents of formula I are useful upon administration to a patient in providing muscular relaxation in the patient during surgery and are normally intravenously administered in a pharmaceutically acceptable carrier.Type: GrantFiled: July 3, 1978Date of Patent: March 11, 1980Assignee: Massachusetts General HospitalInventors: John J. Savarese, Richard J. Kitz, Sara Ginsburg
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Patent number: 4179507Abstract: Compounds of formula (I): ##STR1## wherein Z.sup.1 and Z.sup.2 are the same or different and each represents a methylenedioxy substituent, or up to three methoxy substituents;R.sup.2 and R.sup.3 are the same or different and each is alkyl having 1-3 carbon atoms, prop-2-enyl or prop-2-ynyl;R.sup.4 and R.sup.5 are the same or different and each is a benzyl or phenethyl group wherein the phenyl ring is optionally substituted by one or more of halogen, alkoxy having 1 to 3 carbon atoms and methylenedioxy;A and B are the same or different and each is an alkylene radical containing 1,2, or 3 carbon atoms;L is an alkylene chain having from 2 to 12 carbon atoms or is a group --L.sup.1.0.L.sup.2 -- wherein each of L.sup.1 and L.sup.2 is alkylene having at least two carbon atoms and taken together L.sup.1 and L.sup.2 having up to 11 carbon atoms; andX.sup.- is an anion;may be used to effect neuromuscular paralysis in mammals.Type: GrantFiled: December 9, 1976Date of Patent: December 18, 1979Assignee: Burroughs Wellcome Co.Inventors: John B. Stenlake, Roger D. Waigh, George H. Dewar, John Urwin, Nirmal C. Dhar
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Patent number: 4174447Abstract: A decarboxylation process for coupling aromatic compounds wherein cyclic hydrocarbons and heterocyclic compounds having at least one labile ring hydrogen are reacted with the mono silver salts of aromatic carboxylic acids, or mono silver salts of unsaturated compounds such as .alpha.,.beta.-ethylenically unsaturated acid compounds, or silver trifluoroacetate, or the mono silver salts are reacted with themselves, by heating to temperatures of 100.degree. to 500.degree. C. at pressures of 0.1 to 10 atmospheres, or by irradiating the reactants with ultraviolet light of 200 to 400 nanometers at temperatures of -30.degree. to 150.degree. C. The resulting dimers, trimers, polysubstituted polyphenyls, polyheterocyclics and trifluoromethylated aromatics are useful as heat transfer media, as intermediates for high molecular weight polymers, pesticides and petroleum additives, and as scintillation counters.Type: GrantFiled: February 26, 1975Date of Patent: November 13, 1979Assignee: Standard Oil Company (Indiana)Inventor: Ellis K. Fields
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Patent number: 4163788Abstract: New .alpha.-(cyclic tert. aminophenyl)-aliphatic acids, e.g. those of the formula ##STR1## R.sub.1 =H or alkyl, Ph=a phenylene radical R.sub.2 =H, alk(en)yl, cycloalk(en)yl or cycloalk(en)yl-alkyl ##STR2## =bicyclic alkenyleneimino with 1-3 double bonds AND FUNCTIONAL DERIVATIVES THEREOF, ARE ANTI-INFLAMMATORY AGENTS.Type: GrantFiled: November 7, 1977Date of Patent: August 7, 1979Assignee: Ciba-Geigy CorporationInventors: Richard W. J. Carney, George DE Stevens