Chalcogen Attached Indirectly To The Polycyclo Ring System By Nonionic Bonding Patents (Class 548/260)
  • Patent number: 4845227
    Abstract: This invention provides azole derivatives, their pharmaceutical formulations, and their use in methods of inhibiting aromatase and treating or preventing estrogen-dependent diseases in mammals.
    Type: Grant
    Filed: August 15, 1988
    Date of Patent: July 4, 1989
    Assignee: Eli Lilly and Company
    Inventors: Kenneth S. Hirsch, Charles D. Jones
  • Patent number: 4845180
    Abstract: An ultraviolet absorbing composition comprising a polymer of at least one diisocyantate, at least one polyol and at least one hydroxyl functional, polymerizable ultraviolet absorbing monomer. Included among the preferred ultraviolet absorbing monomers are compounds which have the following structure: ##STR1## and mixtures thereof, wherein X is selected from the group consisting of H, alkoxy radicals and halogen; R.sub.1 is selected from the group consisting of H and alkyl radicals, provided that at least one of X and R.sub.1 is other than H; and R.sub.2 is an organic radical including a functional hydroxyl group.
    Type: Grant
    Filed: March 21, 1988
    Date of Patent: July 4, 1989
    Assignee: Allergan, Inc.
    Inventor: Janis C. Henry
  • Patent number: 4835284
    Abstract: This invention relates to a method for preparing 2-phenylbenzotriazoles having the formula I, ##STR1##
    Type: Grant
    Filed: January 27, 1988
    Date of Patent: May 30, 1989
    Assignee: Chemipro Kasei Kaisha, Ltd.
    Inventor: Shuichi Seino
  • Patent number: 4818273
    Abstract: Novel substituted triazolo[1,5-a]pyrimidine-2-sulfonamides, e.g., 5,7-dimethyl-N-(2,6-dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulf onamide and their agriculturally acceptable salts are prepared. These compounds and compositions containing them are useful for the control of unwanted vegetation. Novel substituted triazolo[1,5-a]pyrimidine-2-sulfonyl chlorides and substituted anilines and their use as intermediates are also described.
    Type: Grant
    Filed: December 10, 1986
    Date of Patent: April 4, 1989
    Assignee: The Dow Chemical Company
    Inventors: William A. Kleschick, Robert J. Ehr, Mark J. Costales, Ben C. Gerwick, III, Richard W. Meikle, deceased, William T. Monte, Pearson, Norman R.
  • Patent number: 4812575
    Abstract: The compound 2(2-hydroxy-5-isopropenylphenyl)2H-benzotriazole (2H5P) is produced by azo coupling of o-nitrophenyl diazonium chloride with p-hydroxyacetophenone, subjecting the resulting isolated azo compound to reductive cyclization with zinc in the presence of sodium hydroxide at a temperature of about 50.degree.-70.degree. C., acidifying the resulting mixture so as to produce (2(2-hydroxy-5-acetylphenyl)2H-benzotriazole (2H5A), acetylating the isolated 2(2-hydroxy-5-acetylphenyl)2H-benzotriazole (2H5A), so as to produce 2(2-acetoxy-5-acetylphenyl)2H-benzotriazole (2A5A), methylating the isolated 2(2-acetoxy-5-acetylphenyl(2H-benzotriazole (2A5A) with a methyl Grignard reagent and dehydrating the isolated reaction product with potassium hydrogen sulfate so as to produce 2(2-hydroxy-5-isopropenylphenyl)2H-benzotriazole (2H5P). The compound is used as a polymerizable ultra violet light stabilizer.
    Type: Grant
    Filed: September 29, 1983
    Date of Patent: March 14, 1989
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Otto Vogl, Zohar Nir
  • Patent number: 4803254
    Abstract: Vinylsilylalkoxy arylbenzotriazol monomers such as 2-[3'-t-butyl-5'-(3-"-dimethylvinylsilylpropoxy)-2'-hydroxy-phenyl]-5-meth oxybenzotriazole are disclosed. These monomers can be incorporated in optically clear silicone polymers to form intraocular lenses, contact lenses, and the like, which have UV absorbing properties.
    Type: Grant
    Filed: March 11, 1987
    Date of Patent: February 7, 1989
    Assignee: Iolab Corporation
    Inventors: Gary B. Dunks, Akira Yamada, Namassivaya Doddi, Charles D. Beard
  • Patent number: 4791206
    Abstract: New reaction products, useful as additives for functional fluids, are obtained by reacting, at elevated temperature,(A) a triazole having the formula IA or IB: ##STR1## wherein R.sub.7 is hydrogen or a C.sub.1 -C.sub.20 alkyl residue;R.sub.8 and R.sub.9 are the same or different and each is C.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.20 alkenyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.7 -C.sub.13 aralkyl, C.sub.6 -C.sub.10 aryl or R.sub.8 and R.sub.9, together with the nitrogen atom to which they are attached, form a 5-, 6- or 7-membered heterocyclic residue or R.sub.8 and R.sub.9 is each a residue of formula:R.sub.12 X[(alkylene)O].sub.n (alkylene)-- IIwherein X is O, S or N(R.sub.12), R.sub.12 is hydrogen or C.sub.1 -C.sub.20 alkyl, "alkylene" is a C.sub.1 -C.sub.12 alkylene residue and n is 0 or an integer from 1 to 6;R.sub.10 is hydrogen, C.sub.1 -C.sub.20 alkyl or C.sub.6 -C.sub.10 aryl or C.sub.7 -C.sub.18 alkyl phenyl; and R.sub.11 is hydrogen, C.sub.1 -C.sub.20 alkyl or a residue --CH.sub.2 NR.sub.8 R.sub.
    Type: Grant
    Filed: May 9, 1986
    Date of Patent: December 13, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert M. O'Neil, Ulrich Kristen, Ulrich Haring
  • Patent number: 4791211
    Abstract: An improved process for the production of 2-stilbylnaphthotriazole optical bleaches which involves diazotizing aminostilbene 2-sulfonic acids, coupling the thus formed diazonium salt with naphthylamino-sulfonic acid to form the stilbylnaphthyl monoazo salt by adding the naphthylamino-sulfonic acid to the diazonium salt from the diazotization, neutralized to a pH in the range of 6-8, in the presence of 2-butoxyethanol, oxidizing said monoazo salt to form the 2-stilbylnaphthotriazole compounds with air in an aqueous alkaline medium containing butoxyethanol and isolating and recovering said 2-stilbylnaphotriazole optical bleaches as their sodium salts.
    Type: Grant
    Filed: January 20, 1987
    Date of Patent: December 13, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Richard B. Lund, Larry W. Bass
  • Patent number: 4788292
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4, independently of one another, represent hydrogen, hydroxy or halogen or are alkyl, alkoxy, alkanoyloxy, or alkanoylamino groups which are unsubstituted or substituted by alkoxy, hydroxyl, halogen, aryl, cycloalkyl, azacycloalkyl, cyano or by polyalkyleneoxy, or two or more of adjacent R.sub.1 -R.sub.4 together form one or more fused rings of 5-8 members each; R is alkylene of up to 16 carbon atoms which is unsubstituted or substituted by hydroxy, lower alkoxy, or halo and which may be interrupted by oxygen, sulfur, carboxamido, sulfonamido, aminosulfonyl, aminocarbonyl, carbonyloxy, sulfinyl, or sulfonyl; and R.sub.f is perfluoroalkyl or perfluoroalkoxyalkyl of 4 to 16 carbon atoms; or mixtures thereof. Such compounds are useful as oil soluble corrosion inhibitors.
    Type: Grant
    Filed: July 31, 1986
    Date of Patent: November 29, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Kirtland P. Clark, Athanasios Karydas
  • Patent number: 4785063
    Abstract: Compounds of the formula I ##STR1## wherein R.sup.1 is hydrogen, chlorine, lower alkyl or lower alkoxy, R.sup.2 is hydrogen or alkyl, R.sup.3 is lower alkenoyl, X and Y are independently --O-- or --NH--, m is 0, 1 or 2 and n is 0 or 1, are suitable as copolymerizable UV stabilizers for polymers obtainable from ethylenically unsaturated monomers. The compounds of the formula I are readily obtainable, and are particularly valuable as UV absorbers by virtue of their good solubility in copolymerizable monomers.
    Type: Grant
    Filed: July 18, 1986
    Date of Patent: November 15, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Mario Slongo, Jean Rody
  • Patent number: 4780541
    Abstract: This invention relates to a method for preparing a 2-phenylbenzotriazole of formula I, ##STR1## (wherein R.sub.1 represents hydrogen or chlorine atom, a lower alkyl group having a carbon number of 1 to 4, a lower alkoxyl group having a carbon number of 1 to 4, carboxyl group, or sulfonic acid group; R.sub.2 represents hydrogen or chlorine atom, a lower alkyl group having a carbon number of 1 to 4, or a lower alkoxyl group having a carbon number of 1 to 4; R.sub.3 represents hydrogen or chlorine atom, an alkyl group having a carbon number of 1 to 12, a lower alkoxyl group having a carbon number of 1 to 4, phenyl group, a phenyl group substituted with an alkyl group having a carbon number of 1 to 8, phenoxy group, or a phenylalkyl group, the alkyl part of which has a carbon number of 1 to 4; R.sub.4 represents hydrogen or chlorine atom, hydroxyl group, or a lower alkoxyl group having a carbon number of 1 to 4; and R.sub.
    Type: Grant
    Filed: September 11, 1986
    Date of Patent: October 25, 1988
    Assignee: Chemipro Kasei Kaisha, Ltd.
    Inventor: Shuichi Seino
  • Patent number: 4769383
    Abstract: A compound of formula (I): ##STR1## or a pharmaceutically acceptable salt thereof, wherein R.sub.1 is a hydrogen atom or a C.sub.1-6 alkyl group, R.sub.2, R.sub.3 and R.sub.4 are the same or different and are selected from hydrogen, hydroxyl, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy and C.sub.1-4 alkanoyl; G is a hydrogen atom or a hydroxyl group, and m and n are independently integers of from 1 to 3, with the proviso that when G is a hydroxyl grup, m or n is 1;is useful in the treatment of asthma.
    Type: Grant
    Filed: September 10, 1986
    Date of Patent: September 6, 1988
    Assignee: Beecham Group p.l.c.
    Inventors: Harry Smith, Derek R. Buckle
  • Patent number: 4760148
    Abstract: 5-alpha-Cumyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole and related 2H-benzotriazoles substituted on the benzo ring by at least one aralkyl group such as benzyl, alpha-methylbenzyl or alpha-cumyl exhibit outstanding efficacy in protecting organic substrates from light-induced deterioration as well as good resistance to loss by volatilization or exudation during the high temperature processing of stabilized compositions. The above-named compounds are surprisingly soluble in common organic solvents, and exhibit very high extinction coefficients.
    Type: Grant
    Filed: September 3, 1985
    Date of Patent: July 26, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Raymond Seltzer, Roland A. E. Winter
  • Patent number: 4755215
    Abstract: A compound of the formula: ##STR1## wherein R is a C.sub.1 -C.sub.5 alkyl group, a C.sub.3 -C.sub.5 alkenyl group, a C.sub.3 -C.sub.5 alkynyl group or a C.sub.3 -C.sub.7 cycloalkyl group, which is useful as a herbicide.
    Type: Grant
    Filed: January 14, 1986
    Date of Patent: July 5, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toru Haga, Eiki Nagano, Ryo Sato, Kouichi Morita
  • Patent number: 4745194
    Abstract: Ultraviolet light absorbing compounds having two different chromophors in the same molecule, particularly the benzotriazole chromophor and either the dihydroxybenzophenone or dihydroxyacetophenone chromophor; specifically, the two compounds 3,5-[di(2H-benzotriazole-2-yl)]-2,4-dihydroxyacetophenone and 3,5-[di(2H-benzotriazole-2-yl)]2,4-dihydroxybenzophenone.
    Type: Grant
    Filed: October 6, 1983
    Date of Patent: May 17, 1988
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Otto Vogl, Shanjun Li
  • Patent number: 4745195
    Abstract: An ultraviolet ray absorbing agent comprising as an active ingredient a spiro compound having a spiro ring structure in the molecule, said spiro compound being represented by the general formula ##STR1## wherein, Y is ##STR2## A is ##STR3## R.sub.1 is hydrogen, halogen, lower alkyl of 1 to 4 carbon atoms, lower alkoxyl of 1 to 4 carbon atoms, carboxyl, or sulfo, R.sub.2 is hydrogen or alkyl of 1 to 12 carbon atoms, R.sub.3 and R.sub.4 are alkyls of 1 to 12 carbon atoms, X is methylene, oxygen, imino, sulfur, sulfinyl, or sulfonyl, and n is an integer of 1 to 12.
    Type: Grant
    Filed: April 28, 1986
    Date of Patent: May 17, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tatsuo Kaneoya, Haruki Okamura
  • Patent number: 4727158
    Abstract: 5-tert-Octyl-2-(2-hydroxy-3,5-di-alpha-cumylphenyl)-2H-benzotriazole and related 2H-benzotriazoles substituted on the 5-position of the benzo ring by a higher alkyl group such as tert-octyl or dodecyl exhibit outstanding efficacy in protecting organic substrates from light-induced deterioration as well as good resistance to loss by volatilization or exudation during the high temperature processing of stabilized compositions. The above-named compounds exhibit good solubility in common organic solvents, and exhibit very high extinction coefficients.
    Type: Grant
    Filed: September 3, 1985
    Date of Patent: February 23, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Raymond Seltzer, Roland A. E. Winter
  • Patent number: 4716234
    Abstract: Ultraviolet light absorbing compositions comprising 2-(2'-hydroxy-5'-acryloyloxyalkoxyphenyl(-2H-benzotrizoles, and copolymers thereof with one or more other monomers copolyermizable therewith, particularly acrylic monomers, are useful in the manufacture of ocular devices, particularly intraocular lenses and contact lenses.
    Type: Grant
    Filed: December 1, 1986
    Date of Patent: December 29, 1987
    Assignee: Iolab Corporation
    Inventors: Gary B. Dunks, Akira Yamada, Charles D. Beard, Namassivaya Doddi
  • Patent number: 4709041
    Abstract: Compounds of the formula ##STR1## wherein R is hydrogen or a hydroxy-protecting group are disclosed. The compounds are versatile intermediates which can be derivatized by reaction of the formyl group to provide a wide variety of ultraviolet-absorbing substituted 2-(2-hydroxyphenyl)-2H-benzotriazoles.
    Type: Grant
    Filed: August 25, 1986
    Date of Patent: November 24, 1987
    Assignee: Polaroid Corporation
    Inventor: Avinash C. Mehta
  • Patent number: 4683071
    Abstract: Mixtures of the compounds of the formulae I and II ##STR1## are metal passivators for functional fluids, such as hydraulic fluids and metal-working fluids in the form of aqueous polyglycol/polyglycol ether mixtures, glycol systems, oil-in-water and water-in-oil emulsions, as well as anti-freeze compositions based on glycol.A process for producing mixtures of the said type is also described.
    Type: Grant
    Filed: October 18, 1985
    Date of Patent: July 28, 1987
    Inventors: Franz Regenass, Peter C. Hamblin
  • Patent number: 4681905
    Abstract: Stabilizer compositions for synthetic resins are provided, improving the resistance of the resin to deterioration when exposed to ultraviolet light, comprising a 2,2,6,6-tetramethylpiperidyl compound and an alkylidene-bis-(benzotriazolyl phenol) having the formula: ##STR1## wherein: R.sub.1 is hydrogen or alkyl having from one to about twelve carbon atoms;R.sub.2 is alkyl having from one to about twelve carbon atoms or arylalkyl having from seven to about sixteen carbon atoms;X is selected from the group consisting of hydrogen, halogen, alkyl having from one to about twelve carbon atoms, aryl having from six to ten carbon atoms, arylalkyl having from seven to about sixteen carbon atoms, alkoxy having from one to about twelve carbon atoms, aryloxy having from six to ten carbon atoms; and arylalkoxy having from seven to about sixteen carbon atoms; as well as synthetic resin compositions containing such stabilizers.
    Type: Grant
    Filed: November 6, 1985
    Date of Patent: July 21, 1987
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Naohiro Kubota, Atsushi Nishimura
  • Patent number: 4675352
    Abstract: Liquid 2-(2-hydroxy-3-higher branched alkyl-5-methylphenyl)-2H-benzotriazole mixtures are prepared by alkylating 2-(2-hydroxy-5-methylphenyl)-2H-benzotriazole with a straight chain alkene or with a branched chain alkene of 8 to 30 carbon atoms in the presence of an acidic catalyst at 100.degree.-200.degree. C. The liquid mixtures exhibit outstanding efficacy in protecting organic substrates from light induced deterioration as well as good resistance to loss by volatilization or exudation during the processing of stabilized compositions at elevated temperatures.
    Type: Grant
    Filed: November 20, 1985
    Date of Patent: June 23, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Roland A. E. Winter, Robert E. Detlefsen
  • Patent number: 4668278
    Abstract: A compound of the formula: ##STR1## wherein R is a hydrogen atom, a C.sub.1 -C.sub.4 alkoxy group, a C.sub.1 -C.sub.4 alkenyloxy group, a C.sub.3 -C.sub.4 alkynyloxy group, a C.sub.1 -C.sub.4 alkylthio group, a dichlorocyclopropylmethoxy group or a methyldichlorocyclopropylmethoxy group, X is a chlorine atom or a bromine atom and Y is a hydrogen atom, a fluorine atom or a chlorine atom, which is useful as a herbicide.
    Type: Grant
    Filed: October 1, 1984
    Date of Patent: May 26, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toru Haga, Eiki Nagano, Masayuki Takase, Ryo Sato
  • Patent number: 4663462
    Abstract: Phenoxy-aminopropanol derivatives of the formula ##STR1## wherein R is lower alkyl, X is oxygen or sulfur, n is the integer zero or 1, Y is methylene, ethylene or propylene or, when n is zero, Y can also be a group of the formula--CH.dbd.CH--C*H.sub.2 --, (a)wherein the double-bond is trans and the carbon atom marked with an asterisk is linked to Z, and Z is a 5-membered aromatic heterocyclic ring which contains one or more nitrogen atoms as the sole hetero atom (s), said heterocyclic ring is linked to Y via a nitrogen atom, and may be substituted by halogen, lower alkyl, lower alkoxy, aryl, cyano or carboxamido, or on adjacent carbon atoms by a group of the formula--(CH.sub.2).sub.4 -- (b)or--CH.dbd.CH--CH.dbd.CH--, (c)and pharmaceutically acceptable acid addition salts thereof are described. A process for the preparation of the compound of formula I and pharmaceutical preparations containing them are also described. The aforementioned compounds and salts possess .beta.
    Type: Grant
    Filed: October 16, 1985
    Date of Patent: May 5, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Peter J. Machin
  • Patent number: 4647563
    Abstract: Compounds of the formula ##STR1## wherein Het is ##STR2## n is an integer from 1 to 4, inclusive, preferably 2 or 3, R.sub.1 is H or acyl,R.sub.2 is H, R.sub.1 O, --NHSO.sub.2 R.sub.7, --NHCOR.sub.8, --NHCONHR.sub.8, --NH--CH.sub.2 --C.sub.6 H.sub.4 --R.sub.9, --CH.sub.2 OH, --CH.sub.2 SO.sub.2 R.sub.7, --CONHR.sub.8, halogen or --CN,R.sub.3 is H, halogen, R.sub.7 or --OR.sub.7,R.sub.2 and R.sub.3 together with each other are ##STR3## R.sub.4 is H, --CH.sub.3 or --C.sub.2 H.sub.5, R.sub.5 and R.sub.6 are each H or --CH.sub.3,R.sub.7 is C.sub.1 -C.sub.4 alkyl,R.sub.8 is H or C.sub.1 -C.sub.4 alkyl,R.sub.9 is H, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy optionally interrupted by oxygen,R.sub.10 and R.sub.12 are each H, CH.sub.3, Cl or OCH.sub.3, or together methylenedioxy,X is ##STR4## or N, and Z is --CH.sub.2 or --CO;in the form of racemates, enantiomers, diastereoisomeric antipode pairs, and non-toxic, pharmacologically acceptable acid addition salts thereof.
    Type: Grant
    Filed: December 9, 1985
    Date of Patent: March 3, 1987
    Assignee: Boehringer Ingelheim KG
    Inventors: Kurt Schromm, Anton Mentrup, Ernst-Otto Renth, Armin Fugner, Ilse Streller
  • Patent number: 4642350
    Abstract: Process for preparing 2-(2'-hydroxyphenyl)-benzotriazoles of the formula ##STR1## from 2-nitro-2'-hydroxyazobenzenes of the formula ##STR2## which comprises reducing a 2-nitro-2'-hydroxyazobenzene compound in a strongly basic medium in the presence of an aromatic dihydroxy or dioxo compound as catalyst and of an alcohol having more than one carbon atom. The 2-(2'-hydroxyphenyl)-benzotriazole compounds are known stabilizers for organic materials.
    Type: Grant
    Filed: December 18, 1985
    Date of Patent: February 10, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Alexander Davatz, Tibor Somlo
  • Patent number: 4611061
    Abstract: The compounds 2'-hydroxy-5'-(hydroxyalkyl)phenyl-2H-benzotriazoles are useful as intermediate alcohols in the preparation of corresponding 2'-hydroxy-5'-acrylyloxyphenyl-2H-benzotriazole monomers, which in turn are copolymerizable with ethylenically unsaturated monomers, particularly acrylic monomers, to impart ultraviolet absorbing properties to the resulting copolymers.
    Type: Grant
    Filed: March 26, 1984
    Date of Patent: September 9, 1986
    Assignee: Iolab Corporation
    Inventors: Charles D. Beard, Namassivaya Doddi, Akira Yamada
  • Patent number: 4587346
    Abstract: Liquid 2-(2-hydroxy-3-higher branched alkyl-5-methylphenyl)-2H-benzotriazole mixtures are prepared by alkylating 2-(2-hydroxy-5-methylphenyl)-2H-benzotriazole with a straight chain alkene or with a branched chain alkene of 8 to 30 carbon atoms in the presence of an acidic catalyst at 100.degree.-200.degree. C. The liquid mixtures exhibit outstanding efficacy in protecting organic substrates from light induced deterioration as well as good resistance to loss by volatilization or exudation during the processing of stabilized compositions at elevated temperatures.
    Type: Grant
    Filed: January 22, 1985
    Date of Patent: May 6, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Roland A. E. Winter, Robert E. Detlefsen
  • Patent number: 4581367
    Abstract: Compounds of the formula whereinHet is a heterocycle;n is an integer from 1 to 4, inclusive, preferably 2 or 3;R.sub.1 is H or acyl;R.sub.2 is H, R.sub.1 O, --NHSO.sub.2 R.sub.7, --NHCOR.sub.8, --NHCONHR.sub.8, --NH--CH.sub.2 --C.sub.6 H.sub.4 --R.sub.9, --CH.sub.2 OH, --CH.sub.2 SO.sub.2 R.sub.7, --CONHR.sub.8, halogen or --CN;R.sub.3 is H, halogen, R.sub.7 or --OR.sub.7 ; orR.sub.2 and R.sub.3, together with each other, are ##STR1## N.sub.4 is H, --CH.sub.3 or --C.sub.2 H.sub.5 ; R.sub.5 and R.sub.6 are each H or --CH.sub.3 ;R.sub.7 is C.sub.1 -C.sub.4 alkyl;R.sub.8 is H or C.sub.1 -C.sub.4 alkyl; andR.sub.9 is H, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy optionally interrupted by oxygen;and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as the salts are useful as bronchospasmolytics, spasmolytics, muscle-relaxants, antiallergics and hypotensives.
    Type: Grant
    Filed: November 23, 1982
    Date of Patent: April 8, 1986
    Assignee: Boehringer Ingelheim KG
    Inventors: Kurt Schromm, Anton Mentrup, Ernst-Otto Renth, Armin Fugner, Ilse Streller
  • Patent number: 4581150
    Abstract: Zwitterionic quaternary ammonium sulfates, and sulfonates are provided as new compounds and as highly effective additives to lubricants and liquid fuels. They have a variety of desirable effects, among them being their ability to reduce friction in an internal combustion engine, thereby reducing the amount of fuel consumed.
    Type: Grant
    Filed: June 5, 1985
    Date of Patent: April 8, 1986
    Assignee: Mobil Oil Corporation
    Inventors: Andrew G. Horodysky, Joan M. Kaminski
  • Patent number: 4560688
    Abstract: Antihistamines of the formula ##STR1## wherein ##STR2## is a 5 or 6 membered ring which is phenyl or heterocyclic; ##STR3## is a six membered ring which is 2,3, or 4 pyridyl or is phenyl or substituted phenyl, with the proviso that is ##STR4## is a nitrogen containing ring, ##STR5## must be phenyl; Z is an alkylene chain having 0 to 2 carbon atoms in the chain, said 2 carbon chain optionally having one double bond, said chain optionally having either a carbonyl oxygen, or a hydroxy group as a substituent; W is ##STR6## wherein p is 1 or 2 and n is 1 or 2, R.sup.1 is C.sub.1 to C.sub.6 alkyl, R.sup.2 is hydrogen or C.sub.1 to C.sub.6 alkyl, and the dotted line represents an optional double bond, R.sup.2 being absent if the double bond is present, and Y is substiuted carboxylate or substituted sulfonyl. Said antihistamines have little or no sedative effects.
    Type: Grant
    Filed: February 8, 1984
    Date of Patent: December 24, 1985
    Assignee: Schering Corporation
    Inventor: Frank J. Villani
  • Patent number: 4560694
    Abstract: Alkylene(cycloalkylene)-bis-heterocyclyl-biguanides of the formula ##STR1## in which A and B each independently is a nitrogen-containing heterocyclic radical which is linked via a nitrogen atom,R is an optionally alkyl-substituted cycloalkylene radical, or an alkylene radical which is optionally substituted by cycloalkylene, bicycloalkylene, tricycloalkylene, oxygen, sulphur or the NR.sup.3 group,R.sup.1 and R.sup.2 each independently is hydrogen, alkyl or optionally substituted aralkyl, orR.sup.1 and R.sup.2 together with the two nitrogen atoms on which they are located and R form a heterocyclic ring, andR.sup.3 is hydrogen, alkyl or optionally substituted aralkyl,or salts thereof which possess fungicidal activity.
    Type: Grant
    Filed: May 20, 1983
    Date of Patent: December 24, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Siegfried Oeckl, Hans-Georg Schmitt, Wilhelm Brandes
  • Patent number: 4548761
    Abstract: Process for the preparation of 1-aminobenzene-2-sulphonic acids of the formula ##STR1## wherein R.dbd.H or a substituent andn=1-4,and their salts, in particular their alkali metal salts, by oxidation of compounds of the formula ##STR2## wherein R.sub.1 .dbd.H, a cation, in particular an alkali metal cation, or a radical of the formula ##STR3## characterized in that the oxidation is carried out in a weakly acidic to alkaline pH range. The process can also be carried out as a one-pot process, using the corresponding benzothiazoles as starting materials.
    Type: Grant
    Filed: June 8, 1983
    Date of Patent: October 22, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Martin Michna, Hermann Henk
  • Patent number: 4482496
    Abstract: The invention relates to stilbene compounds of the formula ##STR1## wherein Q is hydrogen; a monocyclic 5- or 6-membered aromatic heterocyclic ring which is unsubstituted or substituted by non-chromophoric groups and which contains no fused benzene rings or one or two fused benzene rings; a bicyclic 9-membered aromatic heterocyclic ring or the radical --CH.dbd.C(R.sub.1)(R.sub.2), in which R.sub.1 is hydrogen, C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by non-chromophoric groups, and R.sub.2 is alkoxycarbonyl containing altogether 2 to 7 carbons atoms, cyano, carboxyl, carbamoyl, phosphonic acid dialkyl ester, C.sub.1 -C.sub.6 alkyl or arylsulfonyl; or Q may also be ##STR2## R.sub.o is hydrogen or C.sub.1 -C.sub.6 alkyl, R is C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by non-chromophoric groups, C.sub.2 -C.sub.5 alkenyl, C.sub.2 -C.sub.5 alkynyl, di(C.sub.1 -C.sub.4)alkylamino(C.sub.1 -C.sub.4)alkyl, C.sub.1 -C.sub.4 hydroxyalkyl, C.sub.1 -C.sub.
    Type: Grant
    Filed: June 1, 1982
    Date of Patent: November 13, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Kurt Weber
  • Patent number: 4447441
    Abstract: The invention relates to guanidine derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I:- ##STR1## in which R.sup.1 and R.sup.2, same or different, are hydrogen or 1-10C alkyl, 3-8C cycloalkyl or 4-14C cycloalkylalkyl, each alkyl, cycloalkyl or cycloalkylalkyl optionally carrying one or more F, Cl or Br atoms, provided that one of R.sup.1 and R.sup.2 is halogen substituted, or R.sup.2 is hydrogen and R.sup.1 is R.sup.5 --E--W in which W is 2-6C alkylene optionally substituted by 1 or 2 1-4C alkyls, E is O,S or NR.sup.6 in which R.sup.6 is H or 1-6C alkyl, R.sup.5 is H or 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls, or R.sup.5 and R.sup.
    Type: Grant
    Filed: March 1, 1982
    Date of Patent: May 8, 1984
    Assignee: Imperial Chemical Industries PLC
    Inventors: Tobias O. Yellin, David J. Gilman
  • Patent number: 4424360
    Abstract: An improved process for the preparation of fused 1,2,3-triazoles by reaction of an ortho-diaminoaryl with an ester of nitrous acid in a soluent or diluent is disclosed wherein the process is catalyzed by the use of a 1,2,3-triazole.
    Type: Grant
    Filed: March 25, 1982
    Date of Patent: January 3, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ferdinand Hagedorn, Werner Evertz
  • Patent number: 4414393
    Abstract: Ultraviolet-absorbing stabilizers of the formula E-(G-R).sub.n, L-(G-E).sub.m, or [G-E.sub.1 -G-Q].sub.p where E is a radical derived from an oxanilide, benzalmalonate, .alpha.-cyanocinnamate or o-hydroxyphenylbenzotriazole, E.sub.1 is a radical derived from an oxanilide, G is --OCH.sub.2 CHOH--, R is alkyl, phenyl or --CH.sub.2 OT where T is alkyl or alkenyl, n is 1 or 2, m is 2 or 3, L is a direct bond, alkylene or other bis or tris radical, Q has the same meaning as L when m is 2, and p is 1 to 4, are particularly resistant to loss during weathering of outdoor thermoset or thermoplastic coating systems while exhibiting good stabilization efficacy and compatibility in said systems.
    Type: Grant
    Filed: November 5, 1981
    Date of Patent: November 8, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Martin Dexter, Roland A. E. Winter
  • Patent number: 4387100
    Abstract: Phenoxy-aminopropanol derivatives of the formula ##STR1## wherein R is lower alkyl, X is oxygen or sulfur, n is the integer zero or 1, Y is methylene, ethylene or propylene or, when n is zero, Y can also be a group of the formula--CH.dbd.CH--C*H.sub.2 -- (a), wherein the double-bond is trans and the carbon atom marked with an asterisk is linked to Z, and Z is a 5-membered aromatic heterocyclic ring which contains one or more nitrogen atoms as the sole hetero atom (s), said heterocyclic ring is linked to Y via a nitrogen atom, and may be substituted by halogen, lower alkyl, lower alkoxy, aryl, cyano or carboxamido, or on adjacent carbon atoms by a group of the formula ##STR2## and pharmaceutically acceptable acid addition salts thereof are described. A process for the preparation of the compound of formula I and pharmaceutical preparations containing them are also described. The aforementioned compounds and salts possess .beta.-adrenergic blocking activity and antihypertensive activity.
    Type: Grant
    Filed: February 24, 1981
    Date of Patent: June 7, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Peter J. Machin
  • Patent number: 4383863
    Abstract: 2-[2-Hydroxy-3,5-di-tert-octylphenyl]-2H-benzotriazole exhibits outstanding efficacy in protecting organic substrates from light induced deterioration as well as good resistance to loss by volatilization or exudation during the high temperature processing of stabilized compositions.This stabilizer and its 5-chloro analog exhibit great resistance to volatilization, enhanced solubility in selected solvents, desirable absorption characteristics in the ultraviolet range and photographic inertness. This combination of properties makes these benzotriazoles particularly useful in photographic compositions especially in protecting color dye images against the harmful effects of ultraviolet light.
    Type: Grant
    Filed: March 6, 1981
    Date of Patent: May 17, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Martin Dexter, Roland A. E. Winter
  • Patent number: 4380643
    Abstract: A benzotriazole compound of the formula: ##STR1## wherein A is hydrogen or acetyl; R.sup.2 is a C.sub.1 -C.sub.4 alkyl group and n is 1 or 2.
    Type: Grant
    Filed: August 24, 1981
    Date of Patent: April 19, 1983
    Assignee: Asahi Glass Company, Ltd.
    Inventors: Shohei Yoshida, Otto Vogl
  • Patent number: 4379166
    Abstract: This invention relates to 5-(2-alkylamino-1-hydroxyethyl)salicylamides and 4-(2-alkylamino-1-hydroxyethyl)-2-(methylsulfinyl)phenols wherein the alkyl group is substituted by arylmethoxy, arylmethylthio, heteroarylmethoxy, or heteroarylmethylthio, pharmaceutical compositions thereof, and their use as cardiovascular agents.
    Type: Grant
    Filed: August 3, 1981
    Date of Patent: April 5, 1983
    Assignee: Schering Corporation
    Inventors: Bernard R. Neustadt, Elijah H. Gold
  • Patent number: 4378361
    Abstract: Compounds of the formula ##STR1## wherein Het is ##STR2## n is an integer from 1 to 4, inclusive, preferably 2 or 3, R.sub.1 is H or acyl,R.sub.2 is H, R.sub.1 O, --NHSO.sub.2 R.sub.7, --NHCOR.sub.8, --NHCONHR.sub.8, --NH--CH.sub.2 --C.sub.6 H.sub.4 --R.sub.9, --CH.sub.2 OH, --CH.sub.2 SO.sub.2 R.sub.7, --CONHR.sub.8, halogen or --CN,R.sub.3 is H, halogen, R.sub.7 or --OR.sub.7,R.sub.2 and R.sub.3 together with each other are ##STR3## R.sub.4 is H, --CH.sub.3 or --C.sub.2 H.sub.5, R.sub.5 and R.sub.6 are each H or --CH.sub.3,R.sub.7 is C.sub.1 -C.sub.4 alkyl,R.sub.8 is H or C.sub.1 -C.sub.4 alkyl,R.sub.9 is H, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy optionally interrupted by oxygen,R.sub.10 and R.sub.12 are each H, CH.sub.3, Cl or OCH.sub.3, or together methylenedioxy,X is ##STR4## or N, and Z is --CH.sub.2 or --CO;in the form of racemates, enantiomers, diastereoisomeric antipode pairs, and non-toxic, pharmacologically acceptable acid addition salts thereof.
    Type: Grant
    Filed: July 22, 1981
    Date of Patent: March 29, 1983
    Assignee: Boehringer Ingelheim KG
    Inventors: Kurt Schromm, Anton Mentrup, Ernst-Otto Renth, Armin Fugner, Ilse Streller
  • Patent number: 4367337
    Abstract: This invention relates to a process for producing triazoles which comprises effecting a mixture in an aqueous medium of at least one benzimidazolone and one or more nitrites and heating the mixture to temperatures ranging up to about 350.degree. C. while maintaining pressures at levels sufficient to keep effective amounts of water present for the reaction.
    Type: Grant
    Filed: January 5, 1981
    Date of Patent: January 4, 1983
    Assignee: The Sherwin-Williams Company
    Inventor: Frederick W. Sullivan
  • Patent number: 4363914
    Abstract: This invention relates to a process for producing benzotriazoles which comprises effecting a mixture in an aqueous medium of at least one aromatic orthodiamine and one or more nitrites and heating the mixture to temperatures ranging up to about 350.degree. C. while maintaining pressures at levels sufficient to keep effective amounts of water present for the reaction.
    Type: Grant
    Filed: January 5, 1981
    Date of Patent: December 14, 1982
    Assignee: The Sherwin-Williams Company
    Inventors: John W. Long, Lubomir Vacek
  • Patent number: 4359469
    Abstract: N-Sulphenylated oxime-carbamates of the formula ##STR1## in which R is alkyl or optionally substituted cycloalkyl, aryl or aralkyl,R.sup.1 is an optionally substituted N-containing heterocyclic radical or an alkyl or cycloalkyl radical substituted by an optionally substituted N-containing heterocyclic radical,R.sup.2 is alkyl,R.sup.3 is alkyl, halogenoalkyl, optionally substituted phenyl or alkoxycarbonyl, a radical identical to that to which the --(S).sub.n --R.sup.3 group is bonded, or ##STR2## R.sup.4 is alkyl, dialkylamino or optionally substituted phenyl, R.sup.5 is alkyl, andn is 1 or 2,and their salts, which possess arthropodicidal, nematicidal and fungicidal properties.
    Type: Grant
    Filed: July 25, 1977
    Date of Patent: November 16, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jorg Stetter, Bernhard Homeyer, Ingeborg Hammann
  • Patent number: 4353915
    Abstract: 2-(Azol-1-yl)-aldoxime-carbamates of the formula ##STR1## wherein R.sup.1 and R.sup.2 each independently is alkyl or together form an alkylene bridge,R.sup.3 is hydrogen or alkyl,R.sup.4 is hydrogen, alkyl, alkenyl, alkynyl, halogenoalkyl, halogenoalkenyl, alkoxyalkyl or alkylthioalkyl, andAz is azolyl,which possess arthropodicidal and nematicidal properties.
    Type: Grant
    Filed: January 12, 1978
    Date of Patent: October 12, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jorg Stetter, Bernhard Homeyer, Ingeborg Hammann
  • Patent number: 4321396
    Abstract: This invention relates to copolymerizable ultraviolet light absorber compounds having the formula: ##STR1## where R is alkylene, C.sub.1 -C.sub.10, oxyalkylene, C.sub.1 -C.sub.10, alkyleneoxyalkylene, C.sub.1 -C.sub.10 or phenylene, C.sub.1 -C.sub.10, unsubstituted or substituted with hydroxy;R' and R" are independently hydrogen or alkyl; C.sub.1 -C.sub.6 ; andR"' is hydrogen or alkyl, C.sub.1 -C.sub.6.
    Type: Grant
    Filed: December 10, 1980
    Date of Patent: March 23, 1982
    Assignee: GAF Corporation
    Inventors: Donald H. Lorenz, Bruce A. Gruber
  • Patent number: 4310345
    Abstract: New and valuable polycyclic compounds which contain nitrogen-containing rings and have a strong action on plants, agents for influencing plant growth containing these compounds, and a method of influencing plant growth with these compounds.
    Type: Grant
    Filed: January 16, 1980
    Date of Patent: January 12, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Platz, Werner Fuchs, Norbert Rieber, Ulf-Rainer Samel, Johann Jung, Bruno Wuerzer
  • Patent number: 4283327
    Abstract: 2-[2-Hydroxy-3,5-di-tert-octylphenyl]-2H-benzotriazole exhibits outstanding efficacy in protecting organic substrates from light induced deterioration as well as good resistance to loss by volatilization or exudation during the high temperature processing of stabilized compositions.
    Type: Grant
    Filed: August 20, 1979
    Date of Patent: August 11, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Martin Dexter, Roland A. E. Winter
  • Patent number: 4278589
    Abstract: 2-[2-Hydroxy-3,5-di-(.alpha.,.alpha.-dimethylbenzyl)phenyl]-2H-benzotriazol e exhibits outstanding efficacy in protecting organic substrates from light induced deterioration as well as good resistance to loss by volatilization or exudation during the high temperature processing of stabilized compositions. The combination of the benzotriazole UV absorber with a hindered amine light stabilizer is particularly efficacious in protecting thermoset and thermoplastic acrylic resin automotive finishes and enamels.
    Type: Grant
    Filed: May 10, 1979
    Date of Patent: July 14, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Martin Dexter, Roland A. E. Winter