Patents Examined by Sherman D. Winters
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Patent number: 3948939Abstract: Novel 9-aroyl-1,2,3,4-tetrahydrocarbazoles bearing a carboxy substituent at position 3 or 4 and corresponding esters having antiinflammatory activity, the preparation thereof and novel intermediates therefor are described.Type: GrantFiled: October 15, 1974Date of Patent: April 6, 1976Assignee: Sterling Drug Inc.Inventors: Ernest John Alexander, Aram Mooradian
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Patent number: 3947469Abstract: The invention relates to the stereoisomers of novel cyclopentene derivatives and to the preparation thereof.The cyclopentene derivatives are obtained by cycloaddition reaction between cyclopentadiene and a mono-or bis-thioalkyl (or aryl) ketene and reaction between the obtained product and a nucleophile agent.The compounds of the invention are intermediate products valuable for the preparation of different compounds, among which compounds of the prostaglandin type.Type: GrantFiled: September 9, 1974Date of Patent: March 30, 1976Assignee: Recherche et Industrie Therapeutiques (R.I.T.)Inventors: Leon Ghosez, Eric Cossement, Robert Biname
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Patent number: 3946007Abstract: The compounds of the formula ##SPC1##In which R is lower alkyl, lower alkoxy or halo, x is an integer from 0 to 2, n is an integer from 0 to 3, Y is halo and R.sub.1 and R.sub.2 independently are hydrogen, lower alkyl, phenyl or substituted phenyl, or, together with the nitrogen atom, form a heterocyclic ring also containing up to one oxygen atom in the heterocycle. The compounds in which x is 0 are prepared by adding chlorine or bromine to a 1-arylthiomethanesulfonamide in the presence of pyridine to form the 1-arylthio-1, 1-dihalomethanesulfonamide. The compounds in which x is 1 or 2 is prepared by adding sodium hypochlorite or sodium hypobromite to a 1-(arylsulfinyl)methane-sulfonamide or a 1-(arylsulfonyl)methanesulfonamide to form the 1-(arylsulfinyl)-1,1-dihalomethanesulfonamide or 1-(arylsulfonyl)-1,1-dihalomethanesulfonamide, respectively. The compounds are useful as antimicrobial agents.Type: GrantFiled: March 3, 1975Date of Patent: March 23, 1976Assignee: The Dow Chemical CompanyInventors: Christian T. Goralski, Thomas C. Klingler
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Patent number: 3946022Abstract: Compounds of the following general formula are useful as antihistamine agents, antiallergy agents and bronchodilators: ##SPC1##Wherein R represents hydrogen or hydroxy; R.sup.1 represents hydrogen; or R and R.sup.1 taken together form a second bond between the carbon atoms bearing R and R.sup.1 ; n is the integer 4 or 5; Y represents ##EQU1## or ##EQU2## Z represents phenyl or a substituted phenyl ring wherein the substituent on the substituted phenyl ring is attached at the ortho, meta, or para position of the phenyl ring and is selected from halogen, a straight or branched alkyl group of from 1 to 6 carbon atoms, alkoxy of from 1 to 6 carbon atoms, cycloalkyl of from 3 to 6 carbon atoms, di(lower)alkylamino, or a saturated monocyclic heterocyclic group selected from pyrrolidino, piperidino, morpholino or N-(lower)alkyl-piperazino; and pharmaceutically acceptable acid addition salts and individual optical isomers.Type: GrantFiled: March 4, 1974Date of Patent: March 23, 1976Assignee: Richardson-Merrell Inc.Inventors: Albert A. Carr, C. Richard Kinsolving
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Patent number: 3946038Abstract: Certain N,N'-bis(1,1-dioxohydrothienyl)diamino-alkanes, e.g., N,N'-bis(1,1-dioxotetrahydro-3-thienyl)-1,2-diaminopropane, useful as chain extenders for poly-urethanes, especially high resiliency, flexible poly-urethane foams.Type: GrantFiled: November 6, 1974Date of Patent: March 23, 1976Assignee: Uniroyal, Inc.Inventors: Chung-Ling Mao, Lynn A. Bakker
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Patent number: 3944565Abstract: Alkali metal salts of carbazole are prepared by heating carbazole and alkali metal hydroxides with stirring in an organic solvent which forms an azeotrope with water, and removing the resulting water as an azeotrope from the reaction system.The resulting alkali metal salts of carbazole are useful as a material for the preparation of vinyl carbazole for use in electrophotography. The reaction is promoted particularly by the presence of a small amount of water in the reaction system prior to heating.Type: GrantFiled: October 26, 1973Date of Patent: March 16, 1976Assignee: Takasago Perfumery Co., Ltd.Inventors: Hiroshi Otsuki, Kenzo Sakuma, Isamu Matsuzawa
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Patent number: 3944524Abstract: A series of novel 1-piperidinesulfonylurea compounds derived from a nitrogen-containing monocarboxylic acid have been prepared by reacting an appropriate sulfamide with an organic isocyanate or a trisubstituted urea equivalent thereof. The sulfamylureas so obtained are useful in therapy as oral hypoglycemic agents. Typical members include those compounds derived from 2-methoxynicotinic acid, of which 1-(bicyclo[2.2.1]hept-5-en-2-yl-endomethyl)-3-{4-[2-(2-methoxynicotinamido )ethyl]-1-piperidinesulfonyl}urea is a most preferred embodiment.Type: GrantFiled: January 28, 1975Date of Patent: March 16, 1976Assignee: Pfizer Inc.Inventors: George R. Evanega, Donald E. Kuhla, Reinhard Sarges
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Patent number: 3943146Abstract: The disclosed compounds are adducts of imidazole or derivatives thereof and sulfur dioxide. The adducts are apparently of the Lewis acid-Lewis base type, and are useful as latent curing agents for epoxide resins. The adducts are prepared by interacting the imidazole and sulfur dioxide under anhydrous conditions. Equimolar imidazole-SO.sub.2 adducts can serve as a source of sulfur dioxide at room temperature.Type: GrantFiled: February 26, 1974Date of Patent: March 9, 1976Assignee: Minnesota Mining and Manufacturing CompanyInventors: Norman P. Sweeny, Karl Friedrich Thom
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Patent number: 3943154Abstract: Acylamides of .beta.-X-ethenesulfonyl substituted aminoarenes in which the acyl moiety is an organic sulfonic, sulfinic or sulfenic acid group; an organic phosphoric, thiophosphoric, phosphonic, thiophosphonic, or phosphinic acid group; or the sulfinyl group (O=S=). Compounds within the designated class of materials are bioactive, i.e., they control the growth and activity of varying types of plant and animal organisms, e.g., microorganisms or the like.Type: GrantFiled: March 2, 1973Date of Patent: March 9, 1976Assignee: Sanitized IncorporatedInventors: Sven U. K. A. Richter, Alexandros K. Tsolis, Elefteria A. Tsolis
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Patent number: 3941805Abstract: Novel 3-Z-9-benzoyl-1,2,3,4-tetrahydrocarbazoles, wherein Z is CONR.sub.5 R.sub.6, CONHOH, CN, or COCH.sub.2 X, where X is chloro or bromo, having antimicrobial and/or anti-inflammatory activity are disclosed. Compounds wherein Z is CONR.sub.5 R.sub.6 and CONHOH are prepared from the corresponding 3-carboxylic acids by conversion to the corresponding acid chlorides and subsequent reaction with the appropriate amines and hydroxylamine respectively; compounds where Z is CN are prepared by the dehydration of the corresponding compounds where Z is CONH.sub.2 ; and the compounds where Z is COCH.sub.2 X are prepared by reacting hydrogen chloride or bromide with the corresponding compounds where Z is COCHN.sub.2 which in turn is prepared from the corresponding 3-carboxylic acid chloride by reaction with diazomethane.Type: GrantFiled: February 20, 1974Date of Patent: March 2, 1976Assignee: Sterling Drug Inc.Inventor: Ernest John Alexander
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Patent number: 3940402Abstract: Trisaminosulfonium salts of the formula (R.sup.1 R.sup.2 N)(R.sup.3 R.sup.4 N)(R.sup.5 R.sup.6 N)S.sup.+ X.sup.- wherein the R groups are alkyl of 1-20 carbons and each alkyl has at least 2 alpha hydrogens and X is selected from the group (CH.sub.3).sub.3 SiF.sub.2, Cl, Br, I, CN, NCO, NCS NO.sub.2 and N.sub.3, are soluble in organic liquids. They are useful as polymerization catalysts and as reagents to replace other atoms or groups in organic compounds with F, Cl, Br, I, CN, NCO, NCS, NO.sub.2 or N.sub.3.Type: GrantFiled: September 19, 1974Date of Patent: February 24, 1976Assignee: E. I. DuPont de Nemours and CompanyInventor: William Joseph Middleton
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Patent number: 3940401Abstract: 4-Piperidone ketal derivatives of the formulae ##SPC1##And ##SPC2##Wherein R.sub.1 represents an alkyl group of 1 to 8 carbon atoms and R.sub.2 represents an alkylene group of 2 or 3 carbon atoms or o-phenylene group and they are prepared by reacting triacetonamine with a monohydric alcohol of the formulaR.sub.1 --OH (III)wherein R.sub.1 is as defined above or a dihydric alcohol or phenol of the formulaR.sub.2 --(OH).sub.2 (IV)wherein R.sub.2 is as defined above in the presence of an acid catalyst. They are useful as statilizers against deterioration of synthetic polymers.Type: GrantFiled: July 24, 1974Date of Patent: February 24, 1976Assignee: Sankyo Company LimitedInventors: Keisuke Murayama, Toshimasa Toda, Eiko Mori, Katsuaki Matsui, Tomoyuki Kurumada, Noriyuki Onta, Ichiro Watanabe
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Patent number: 3939177Abstract: Novel 4-R.sub.1 R.sub.2 NCH.sub.2 -9-benzyl-6-R.sub.3 -7-R.sub.4 -1,2,3,4-tetrahydrocarbazoles having antibacterial activity are disclosed. The compounds are prepared by the chemical reduction of the corresponding 4-R.sub.1 R.sub.2 NCO-9-benzyl-6-R.sub.3 -7-R.sub.4 -1,2,3,4-tetrahydrocarbazoles.Type: GrantFiled: November 22, 1972Date of Patent: February 17, 1976Assignee: Sterling Drug Inc.Inventors: Ernest John Alexander, Aram Mooradian
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Patent number: 3939167Abstract: A phenylisoxazole of the formula: ##SPC1##Wherein, Y represents a hydrogen atom, a halogen atom, an alkali metal atom or a tertiary amino group and Z represents a sulfur atom or a sulfoxide group. They are prepared by subjecting 3-alkoxycarbonyl-5-phenylisoxazole to a treatment with at least one agent selected from the group consisting where required and as necessary of dimethyl sulfoxide, a neutralizing agent, an agent capable of releasing a halogen ion and a secondary amine at a temperature ranging from about -5.degree.C to about 70.degree.C for a time period from several minutes up to about 4 hours.The phenylisoxazoles are useful as intermediates for preparing a 3-(2-tertiary amino-1-hydroxyethyl)-5-phenylisoxazole, any of which is known as useful medicaments having a remarkable analgesic, antispasmodic, antiphretic, antiallergic, antiinflammatory, antitussive activity or the like, each reflecting the species of the substituent tertiary amino groups and generally having a very low toxicity.Type: GrantFiled: August 21, 1973Date of Patent: February 17, 1976Assignee: Shionogi & Co., Ltd.Inventors: Shoichi Hirai, Kyozo Kawata
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Patent number: 3939168Abstract: New piperidine derivatives and in particular esters and amides of substituted (piperidinyl-4) acetic acid are used as stabilisers for polymers, especially for polyolefines.Type: GrantFiled: July 17, 1973Date of Patent: February 17, 1976Assignee: Ciba-Geigy CorporationInventor: Barry Cook
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Patent number: 3937711Abstract: New piperidine derivatives and in particular 2-(piperidinyl-4')-ethyl-amines, -ethers and -esters are used as stabilisers for polymers, especially for polyolefines.Type: GrantFiled: October 15, 1973Date of Patent: February 10, 1976Assignee: Ciba-Geigy CorporationInventor: Barry Cook
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Patent number: 3936468Abstract: Butyrophenone derivatives having excellent psychotropic activity and represented by the formula, ##SPC1##Wherein A represents a single or double bond linkage; R.sub.1 represents a hydrogen atom or a C.sub.1 - C.sub.4 alkyl group; R.sub.2, which is present only in case A represents a single bond linkage, represents a hydrogen atom, or a hydroxyl, C.sub.1 - C.sub.4 alkyl, or C.sub.1 - C.sub.4 alkoxy group; R.sub.3 represents a hydrogen atom, or a piperidino, pyrrolidino, morpholino, furyl, thienyl, C.sub.1 - C.sub.4 alkylamino, benzylamino, unsubstituted or halogen-substituted phenyl group, etc.; and X represents a hydrogen or halogen atom, or a C.sub.1 - C.sub.4 alkyl, C.sub.1 - C.sub.4 alkoxy, or trifluoromethyl group, can be prepared by reducing a benzoylpropionamide derivative of the formula, ##SPC2##Wherein A, R.sub.1, R.sub.2, R.sub.Type: GrantFiled: February 15, 1973Date of Patent: February 3, 1976Assignee: Sumitomo Chemical Company, Ltd.Inventors: Hisao Yamamoto, Masaru Nakao, Kikuo Sasajima, Isamu Maruyama, Shigenari Katayama
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Patent number: 3936462Abstract: 1,2,3,4,5,6-Hexahydro-1-oxo-3-(hydrocarbon or substituted hydrocarbon)-8-(H or OH)-6-(H or alkyl)-11-(H or alkyl)-2,6-methano-3-benzazocines and 1-hydroxy secondary and tertiary alcohols obtainable therefrom by reduction and by Grignard reactions, and esters of the same, are useful as central nervous system depressants, particularly as analgesics and as analgesic antagonists. The 3-substituent is introduced by alkylation, directly or by N-acylation followed by reduction of the resulting amides, of the corresponding >NH compounds either before or after introduction of the 1-oxo group into the compounds having two hydrogens at the 1-position by chromium (VI) oxidation. Various intermediates and derivatives are also descibed, including 3a,4,5,9b-tetrahydro-3,5-ethanonaphth[2,1-d]oxazol-2(3H)-ones obtained by interacting 1,2,3,4,5,6-hexahydro-1-hydroxy-2,6-methano-3-benzazocines with phosgene or by heating 1,2,3,4,5,6-hexahydro-1-hydroxy-3-carbalkoxy-2,6-methano-3-benzazocines with alkoxide ion.Type: GrantFiled: June 14, 1973Date of Patent: February 3, 1976Assignee: Sterling Drug Inc.Inventor: Noel F. Albertson
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Patent number: 3936466Abstract: There is provided, novel 3-chloro-tetrahydro 1,3-oxazine or oxazolidine compounds, exhibiting antibacterial activity and being of low chlorine potential of the formula: ##EQU1## WHEREIN EACH OF R.sub.1 and R.sub.2, which may be the same or different, represent an alkyl group of from 1 to 20 carbon atoms (C.sub.1 -C.sub.5 being preferred); wherein each of R.sub.5 and R.sub.6, which may be the same or different, represent a hydrogen atom or an alkyl group of from 1 to 20 carbon atoms (C.sub.1 -C.sub.5 being preferred); wherein l represents an integer of 1 or 2 and wherein each of R.sub.3 and R.sub.4, which may be the same or different, represent an alkyl group of from 1 to 20 carbon atoms (C.sub.1 -C.sub.5 being preferred), a --(CH.sub.2).sub.n X group, wherein n represents an integer of from 1 to 20 and wherein X represents a dimethylamino group, a diethylamino group, a trimethylammonium group, a triethylammonium group, a dimethylammonium group, a diethylammonium group, a --COOR.sub.7 group, a --OOCR.sub.Type: GrantFiled: April 10, 1975Date of Patent: February 3, 1976Assignee: Interx Research CorporationInventors: Nicolae S. Bodor, James J. Kaminski
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Patent number: 3936467Abstract: New .alpha.-(cyclic tert. aminophenyl)-aliphatic acids, e.g. those of the formula ##SPC1##R.sub.1 = h or alkylR.sub.2 = h, alk(en)yl, cycloalk(en)- yl or cycloalk(en)yl-alkylA = hydroxylated lower alkyleneAnd functional derivatives thereof, are anti-inflammatory agents.Type: GrantFiled: March 25, 1974Date of Patent: February 3, 1976Assignee: Ciba-Geigy CorporationInventors: Richard William James Carney, George DE Stevens