Oxy Containing Patents (Class 568/442)
  • Patent number: 4542237
    Abstract: .alpha.-Arylalkanoic acids or esters, orthoesters or amides thereof are prepared by forming an .alpha.-hydroxy ketal or thioketal of an aryl alkyl ketone, activating the .alpha.-hydroxy substituent with an esterifying agent to form the corresponding ketal or thioketal ester substrate, wherein the ester group is sufficiently labile to non-catalytically disassociate from the substrate in a protic or dipolar, aprotic solvent, maintaining the ester substrate in contact with the protic or dipolar, aprotic solvent or mixtures thereof for a time sufficient to form the corresponding .alpha.-arylakanoic acid or ester, orthoester or amide thereof, and optionally concomitantly or sequentially hydrolyzing any ester, orthoester or amide formed to the corresponding .alpha.-arylalkanoic acid.
    Type: Grant
    Filed: June 7, 1983
    Date of Patent: September 17, 1985
    Assignee: Syntex Pharmaceuticals International Limited
    Inventor: George C. Schloemer
  • Patent number: 4540827
    Abstract: Herbicidally active compounds of the formula ##STR1## in which .sup.1 represents a hydrogen or chlorine atom,R.sup.2 represents a hydrogen atom, a cyano group, an optionally substituted radical selected from alkyl, aryl, alkanoyl, benzoyl, alkoxycarbonyl, alkenoxycarbonyl, alkinoxycarbonyl, aralkoxycarbonyl and aryloxycarbonyl, or a radical of the general formula --COOM,in whichM represents a hydrogen atom, one equivalent of an alkali metal ion or alkaline earth metal ion or optionally substituted ammonium, andR.sup.3 represents a cyano group or a radical of the general formula ##STR2## wherein Y represent an oxygen or sulphur atom or an imino (NH) or alkylimino (Nalkyl) group,R.sup.4 and R.sup.5 independently of each other represent a hydrogen atom or a methyl group,n is 0 or 1 andZ represents an optionally substituted radical.Novel intermediates therefor are also shown.
    Type: Grant
    Filed: June 1, 1984
    Date of Patent: September 10, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Forster, Ludwig Eue, Robert Schmidt
  • Patent number: 4537996
    Abstract: New hydroxybiphenyl compounds of the general formula: ##STR1## wherein R.sub.1 stands for a hydrogen atom or a hydroxyl group, R.sub.2 for a hydrogen atom or a hydroxyl group, R.sub.3 for a hydroxyl group, a group of the formula -CH.sub.2 -CH.dbd.CH.sub.2 or a group of the formula -CH.dbd.CH-CHO, R.sub.4 for a hydrogen atom or a group of the formula ##STR2## and R.sub.5 for a hydroxyl group or a group of the formula ##STR3## These compounds are obtained by extraction of "Tokoboku", i.e. dried cortex of Magnolia officinalis which belongs to the family Magnoliaceae. They are useful as pharmaceuticals or intermediates therefor, in particular as anti-allergics.
    Type: Grant
    Filed: September 22, 1983
    Date of Patent: August 27, 1985
    Assignee: Kabushiki Kaisha Tsumurajuntendo
    Inventors: Akihide Kooda, Itsuo Nishioka, Takeshi Nishiyori, Shoji Yahara
  • Patent number: 4532364
    Abstract: Described are ether carboxaldehydes defined according to the generic structure: ##STR1## wherein X represents aryl, alkaryl, hydroxyalkyl, alkenyl, cycloalkenyl, lower alkyl or bicycloalkyl; wherein Y represents C.sub.1 -C.sub.3 lower alkylene; wherein Z completes an alkyl substituted C.sub.6 cycloalkyl ring or represents no moiety; wherein R represents hydrogen or methyl; wherein m represents 0 or 1; wherein n represents 0 or 1; wherein p represents 0 or 1 and wherein q represents 0 or 1 with the provisos that when m is 1, Z completes the alkyl substituted or unsubstituted C.sub.
    Type: Grant
    Filed: September 19, 1983
    Date of Patent: July 30, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
  • Patent number: 4524032
    Abstract: A process for direct fluorination of etherified or unetherified hydroxy group-bearing aromatic compounds, which comprises reacting an etherified or unetherified hydroxy group-bearing aromatic compound with fluorine gas to give the corresponding etherified or unetherified hydroxy group and at least one fluorine atom-bearing aromatic compound.
    Type: Grant
    Filed: January 14, 1983
    Date of Patent: June 18, 1985
    Assignee: Daikin Kogyo Co., Ltd.
    Inventors: Susumu Misaki, Sadamu Ishii, Masahiro Suefuji
  • Patent number: 4523037
    Abstract: By reacting, using as a catalyst a modified or unmodified cyclodextrin, a phenol compound with a haloform in the presence of an alkali metal hydroxide, while maintaining the molar ratio of the cyclodextrin to the haloform at 0.5 to 10, a substituent group derived from the haloform can be introduced to the para-position of the phenol compound with high selectivity, whereby useful para-substituted phenol derivatives can be advantageously obtained.
    Type: Grant
    Filed: September 7, 1983
    Date of Patent: June 11, 1985
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Hidefumi Hirai, Makoto Komiyama
  • Patent number: 4521634
    Abstract: Described are ether carbinols defined according to the generic structure: ##STR1## wherein X.sub.1 represents a moiety selected from the group consisting of: ##STR2## and wherein Y.sub.1 represents C.sub.4 or C.sub.5 alkylene or C.sub.4 or C.sub.5 alkenylene or C.sub.4 or C.sub.5 alkynylene; processes for preparing such ether carbinols by means of first reacting allyl ethers with a mixture of carbon monoxide and hydrogen by means of an oxoreaction to produce ether carboxaldehydes and then reducing the thus formed ether carboxaldehydes to ether carbinols; or reacting camphene with appropriate diols; as well as methods for augmenting or enhancing the aroma or taste of consumable materials including perfumes, colognes and perfumed articles; foodstuffs, chewing gums, chewing tobaccos, medicinal products and toothpastes; and smoking tobaccos and smoking tobacco articles by adding thereto an aroma or taste augmenting or enhancing quantity of the thus produced ether carbinols.
    Type: Grant
    Filed: January 26, 1984
    Date of Patent: June 4, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
  • Patent number: 4518797
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO,--C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.
    Type: Grant
    Filed: March 15, 1979
    Date of Patent: May 21, 1985
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman
  • Patent number: 4515987
    Abstract: Described is a genus of compounds defined according to the structure: ##STR1## (Z) represents one of the moieties ##STR2## as well as the substantially pure compound defined according to the structure: ##STR3## and the use thereof for augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, medicinal products, toothpastes, chewing tobaccos, smoking tobaccos, smoking tobacco articles, perfumes, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, fabric softener articles, perfumed articles, hair preparations and the like.
    Type: Grant
    Filed: June 26, 1984
    Date of Patent: May 7, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Theodore J. Tyszkiewicz, Michael Licciardello, Manfred H. Vock, Joaquin F. Vinals, Patrick Whalen, Marie R. Hanna
  • Patent number: 4508925
    Abstract: There is disclosed a novel process for preparing a number of cinnamaldehyde derivatives. These cinnamaldehyde derivatives can be reduced to dihydrocinnamaldehyde derivatives, a number of which are commercially important in the preparation of fragrances. The invention is also directed to a number of novel intermediates and their preparation.
    Type: Grant
    Filed: November 9, 1983
    Date of Patent: April 2, 1985
    Assignee: Givaudan Corporation
    Inventors: Yvo Crameri, Paul A. Ochsner, Peter Schudel
  • Patent number: 4491537
    Abstract: Described are tertiary hydroxyl carboxaldehydes defined according to the generic structure: ##STR1## wherein the lines* * * * *and-- -- -- -- -- --and/or+ + + + +represent covalent carbon-carbon bonds when m does not=0; and wherein the lines+ + + + +* * * * *and-- -- -- -- -- --do not represent any bonds when m=0; wherein R represents hydrogen or methyl; wherein p and q each represents 0 or 1 with the proviso that p=1 when q=0 and p=0 when q=1; wherein X and Z each represent one or more carbon atoms required to complete a bicyclo ring with the lines+ + + + +* * * * *and-- -- -- -- -- --representing carbon-carbon bonds; wherein X and Z complete a phenyl moiety when the line-- -- -- -- -- --represents no bond; wherein X and Z complete a cycloalkyl ring moiety with the lines* * * * *and+ + + + +represent carbon-carbon bonds and with the line-- -- -- -- -- --representing no bond; and wherein when m is 0, X represents an alkylene moiety, processes for preparing same by means of reacting carbon monoxide and hydroge
    Type: Grant
    Filed: July 8, 1983
    Date of Patent: January 1, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
  • Patent number: 4482736
    Abstract: Herbicidally active compounds of the formula ##STR1## in which R.sup.1 represents a hydrogen or chlorine atom,R.sup.2 represents a hydrogen atom, a cyano group, an optionally substituted radical selected from alkyl, aryl, alkanoyl, benzoyl, alkoxycarbonyl, alkenoxycarbonyl, alkinoxycarbonyl, aralkoxycarbonyl and aryloxycarbonyl, or a radical of the general formula--COOM,in whichM represents a hydrogen atom, one equivalent of an alkali metal ion or alkaline earth metal ion or optionally substituted ammonium, andR.sup.3 represents a cyano group or a radical of the general formula ##STR2## wherein Y represents an oxygen or sulphur atom or an imino (NH) or alkylimino (Nalkyl) group,R.sup.4 and R.sup.5 independently of each other represent a hydrogen atom or a methyl group,n is 0 or 1 andZ represents an optionally substituted radical,Novel intermediates therefor are also shown.
    Type: Grant
    Filed: July 14, 1983
    Date of Patent: November 13, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Forster, Ludwig Eue, Robert Schmidt
  • Patent number: 4457939
    Abstract: A series of 5-(2-alkoxy-3-substituted phenyl)hydantoins and pharmaceutically acceptable salts thereof useful as aldose reductase inhibitors and as therapeutic agents for the treatment of chronic diabetic complications; intermediates therefore; and processes for preparation of said compounds.
    Type: Grant
    Filed: November 1, 1982
    Date of Patent: July 3, 1984
    Assignee: Pfizer Inc.
    Inventor: Rodney C. Schnur
  • Patent number: 4454330
    Abstract: A process for the preparation of a two-functional-group-containing terpenoid having the general formula: ##STR1## in which n is an integer of from 1 to 5, R represents a hydroxymethyl, formyl or carboxyl group, and A represents the hydrogen atom, or a 2-tetrahydropyranyl, benzyl, methoxymethol or methoxyethoxymethyl group comprising the oxidation with a microorganism belonging to the genus Nocardia. Some of the terpenoids are of value as anti-ulcer agents, while others are useful as intermediates.
    Type: Grant
    Filed: March 22, 1982
    Date of Patent: June 12, 1984
    Assignees: Eisai Co., Ltd., General Director of the Agency of Industrial Science and Technology
    Inventors: Akio Sato, Kenji Nakajima, Yoshimasa Takahara, Shizumasa Kijima, Noriaki Kuwana, Shinya Abe, Kouzi Yamada
  • Patent number: 4452994
    Abstract: An improved process for isolating organic compounds from crude product or reaction mixtures by dissolving said crude product or reaction mixture in a suitable solvent, contacting the resulting solution with a lithium salt to form a solid metal salt complex, separating, and thereafter recovering a pure product by decomposing the lithium salt complex.
    Type: Grant
    Filed: March 2, 1981
    Date of Patent: June 5, 1984
    Assignee: G. D. Searle & Co.
    Inventors: John B. Hill, Robert A. Erickson
  • Patent number: 4435585
    Abstract: There is disclosed a novel process for preparing a number of cinnamaldehyde derivatives. These cinnamaldehyde derivatives can be reduced to dihydrocinnamaldehyde derivatives, a number of which are commercially important in the preparation of fragrances. The invention is also directed to a number of novel intermediates and their preparation.
    Type: Grant
    Filed: November 17, 1981
    Date of Patent: March 6, 1984
    Assignee: Givaudan Corporation
    Inventors: Yvo Crameri, Paul A. Ochsner, Peter Schudel
  • Patent number: 4430354
    Abstract: Described is a genus of compounds defined according to the structure: ##STR1## (Z) represents one of the moieties ##STR2## as well as the substantially pure compound defined according to the structure: ##STR3## and the use thereof for augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, medicinal products, toothpastes, chewing tobaccos, smoking tobaccos, smoking tobacco articles, perfumes, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, fabric softener articles, perfumed articles, hair preparations and the like.
    Type: Grant
    Filed: May 20, 1983
    Date of Patent: February 7, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Theodore J. Tyszkiewicz, Michael Licciardello, Manfred H. Vock, Joaquin F. Vinals, Patrick Whalen, Marie R. Hanna
  • Patent number: 4418206
    Abstract: Novel compounds of the formula: ##STR1## wherein A is CHOH, CHO or COOR; R is hydrogen or a lower alkyl group of 1 to 4 carbon atoms; and the pharmaceutically acceptable, non-toxic salts of compounds in which R is hydrogen; and X is hydrogen, o-, m- or p-halo(fluoro, chloro or bromo), o-, m- or p-methyl or o-, m- or p-methoxy. These compounds possess prostaglandin-like activity and thus are useful in the treatment of mammals where prostaglandins are indicated. They are particularly useful as inhibitors of gastric acid secretions and as agents for the control of asthmatic attack, because of their bronchodilating activity.
    Type: Grant
    Filed: March 22, 1982
    Date of Patent: November 29, 1983
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Douglas L. Wren
  • Patent number: 4408070
    Abstract: Pure crystalline racemic sodium parahydroxymandelate free from any ions of chloride, acetate, formate and sulfate group, is manufactured by condensing in water, in the presence of sodium hydroxide at a temperature between 30.degree. and 100.degree. C., glyoxylic acid or sodium glyoxylate with an excess of phenol, concentrating it hot, until the start of crystallization of the solution thus obtained after neutralization and removal of the unconverted phenol either by steam distillation, or by extraction with a water-immiscible organic solvent. The resulting suspension obtained is cooled, drained after some hours of standing at a temperature close to 5.degree. C., and the resulting precipitate recovered by washing it with iced water followed by drying to constant weight. The product is useful for the manufacture of crystalline sodium paraformylphenolate.
    Type: Grant
    Filed: July 20, 1981
    Date of Patent: October 4, 1983
    Inventors: Alain Schouteeten, Yani Christidis
  • Patent number: 4395575
    Abstract: 9-Substituted, 4- or 6-fluorine substituted retinoic acid derivatives useful as antitumor agents and in the treatment of acne as well as a method for their manufacture are disclosed. Substituents at the 9-position include substituted phenyl, thienyl and furyl groups.
    Type: Grant
    Filed: March 3, 1982
    Date of Patent: July 26, 1983
    Assignee: Hoffmann-La Roche, Inc.
    Inventors: Ka-Kong Chan, Beverly A. Pawson
  • Patent number: 4371547
    Abstract: 2-Benzylideneglutaraldehydes of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently are hydrogen or a substituent selected from the group consisting of halo, lower-alkyl, phenyl, carboxy, lower-alkoxycarbonyl, phenoxycarbonyl, aminocarbonyl, hydroxysulfonyl, nitro, cyano, hydroxy, lower-alkoxy and phenoxy, a method of use thereof as disinfectants, disinfectant compositions comprising them, and 2,6-dialkoxy-3-(.alpha.-alkoxybenzyl)tetrahydropyrans of the formula ##STR2## where R.sup.1, R.sup.2 and R.sup.3 are as defined above and R.sup.4 and R.sup.5 independently are alkyl of one to four carbon atoms, which are intermediates for their preparation are disclosed.
    Type: Grant
    Filed: August 21, 1981
    Date of Patent: February 1, 1983
    Assignee: Sterling Drug Inc.
    Inventors: Wolfgang Munzenmaier, Heinz Eggensperger, Helmut H. Ehlers, Wolfgang Beilfuss, Lothar Bucklers, Hans-Peter Harke
  • Patent number: 4371712
    Abstract: An alkyl-substituted salicylaldehyde whose alkyl-substituent contains at least 6 and up to 2000 or more carbon atoms are novel composition of matter. Said novel alkylsalicylaldehyde can be prepared by the novel reaction of an alkylphenol containing at least six carbon atoms and up to 2000 or more carbon atoms in the phenol's alkyl-substituent, a dialkyloxy methane and a peroxide in the presence of a free radical forming catalyst.
    Type: Grant
    Filed: October 22, 1981
    Date of Patent: February 1, 1983
    Assignee: Standard Oil Company (Indiana)
    Inventors: Richard J. Lee, Leonard J. Baranowski
  • Patent number: 4351950
    Abstract: Novel substituted arylene compounds and methods for their preparation and use are disclosed. These new compounds are useful as anti-arteriosclerotic agents.
    Type: Grant
    Filed: January 2, 1980
    Date of Patent: September 28, 1982
    Assignee: Warner-Lambert Company
    Inventor: Ila Sircar
  • Patent number: 4351962
    Abstract: A process is provided for the preparation of hydroxy benzene carboxaldehydes having the formula: ##STR1## wherein: R is selected from the group consisting of alkyl, alkoxy, cycloalkyl, aryl, alkoxyalkyl, fluoroalkyl, and hydroxyalkyl oxyalkylene having from one to about twenty carbon atoms; hydroxyalkyl having at least two to about twenty carbon atoms; hydroxy; aldehyde CHO; and halogen;n.sub.1, n.sub.2 and n.sub.3 are zero or 1; and at least one of n.sub.1, n.sub.2 and n.sub.3 is 1; andx is zero, 1, 2, 3 or 4, which comprises:(1) condensing with a formaldehyde compound a phenol having the formula: ##STR2## wherein R is selected from the group consisting of alkyl, alkoxy, hydroxyalkyl, cycloalkyl, aryl, alkoxyalkyl, fluoroalkyl, and hydroxyalkyl oxyalkylene having from one to about twenty carbon atoms; hydroxy; and halogen; andx is zero, 1, 2, 3 or 4,and unsubstituted in at least one ortho or para position in an aqueous reaction medium comprising phenol:HCHO in a molar ratio within the range from about 1:0.
    Type: Grant
    Filed: July 11, 1980
    Date of Patent: September 28, 1982
    Assignee: Rhone Poulenc Inc.
    Inventors: Peter S. Gradeff, Stanley T. Murayama
  • Patent number: 4350833
    Abstract: Terephthaldialdehyde monoacetals represented by the general formula: ##STR1## (wherein, R.sub.1 and R.sub.2 are lower alkyl groups) are novel compounds, and they are produced by the reaction of terephthaldialdehyde with alcohols in the presence of a strongly acidic substance as a catalyst.
    Type: Grant
    Filed: January 28, 1981
    Date of Patent: September 21, 1982
    Inventor: Kunihiro Ichimura
  • Patent number: 4346238
    Abstract: Sodium paraformylphenolate crystallized with two molecules of water is manufactured by:(a) condensing glyoxylic acid with an excess of phenol in water in the presence of sodium hydroxide at a temperature comprised between 30.degree. C. and 100.degree. C.;(b) neutralizing the solution thus obtained and then freeing it from the unconverted phenol by steam distillation or extraction with a water-immiscible organic solvent and then subjecting it hot under a pressure of oxygen, to a catalytic decarboxylating oxidizing degradation in the presence of sodium hydroxide;(c) allowing the aqueous solution so-obtained, after removal of the catalyst by filtration, and then concentration hot under vacuum to 60% plus or minus 10% of its initial volume, to crystallize; and(d) draining the precipitated crystals, washing them and then drying them to constant weight under vacuum of 1 mm of mercury at 20.degree. C.
    Type: Grant
    Filed: May 7, 1980
    Date of Patent: August 24, 1982
    Assignee: Societe Francaise Hoechst
    Inventors: Alain Schouteeten, Yani Christidis
  • Patent number: 4340765
    Abstract: 4-Phenoxy-2-butene derivatives are disclosed as inhibitors of cytokinin plant growth regulatory activity and as possessing seed germination regulatory properties and senescence delaying activity when applied to plants. 4-Phenoxy-2-butene derivatives can also be useful as plant dwarfing agents, agents to retard seedling development or as herbicides.
    Type: Grant
    Filed: August 14, 1980
    Date of Patent: July 20, 1982
    Inventors: Gary M. Gray, George Schwartzkopf, Jr., J. T. Baker Chemical Co.
  • Patent number: 4338251
    Abstract: A process for the preparation of a two-functional-group-containing terpenoid having the general formula: ##STR1## in which n is an integer of from 1 to 5, R represents a hydroxymethyl, formyl or carboxyl group, and A represents the hydrogen atom, or a 2-tetrahydropyranyl, benzyl, methoxymethol or methoxyethoxymethyl group comprising the oxidation with a microorganism belonging to the genus Nocardia. Some of the terpenoids are of value as anti-ulcer agents, while others are useful as intermediates.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: July 6, 1982
    Assignees: Eisai Co., Ltd., Agency of Industrial Science and Technology
    Inventors: Akio Sato, Kenji Nakajima, Yoshimasa Takahara, Shizumasa Kijima, Noriaki Kuwana, Shinya Abe, Kouzi Yamada
  • Patent number: 4337346
    Abstract: An optically active or racemic .alpha.-hydroxyaldehyde represented by the general formula (2), ##STR1## wherein R.sub.1 represents a C.sub.6 -C.sub.14 aryl group, C.sub.1 -C.sub.10 alkyl group, C.sub.3 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7 -C.sub.14 aralkyl group, or a group containing a functional group in the organic portion of said groups and R.sub.2 represents a C.sub.1 -C.sub.10 alkyl group, C.sub.2 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7-C.sub.14 aralkyl group, C.sub.6 -C.sub.14 aryl group, or a group containing a functional group in the organic portion of these groups, which is an important intermediate for preparation of pharmaceuticals and agricultural chemicals, and prepared by allowing an optically active or racemic compound represented by the general formula (1), ##STR2## (wherein A represents a C.sub.6 -C.sub.14 aryl group or a C.sub.1 -C.sub.4 alkyl or alkoxy group- or halogen-substituted C.sub.6 -C.sub.14 aryl group and R.sub.
    Type: Grant
    Filed: October 30, 1979
    Date of Patent: June 29, 1982
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Teruaki Mukaiyama, Yoji Sakito, Masatoshi Asami
  • Patent number: 4336268
    Abstract: Cyclohexenes of the formula ##STR1## wherein R.sup.1 is hydroxy or lower alkoxy; n is 1 or 2; R.sup.2 is lower alkyl; and R.sup.3 is hydrogen, lower alkyl, lower alkenyl or lower cycloalkylmethyl, and their pharmaceutically acceptable acid addition salts are disclosed. The compounds of formula I have analgesic activity and are useful for the control of pains.
    Type: Grant
    Filed: January 27, 1981
    Date of Patent: June 22, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Hans Bruderer, Albert E. Fischli, Rudolf Pfister
  • Patent number: 4333952
    Abstract: Compounds of formula (I): ##STR1## wherein: R.sup.1 is hydrogen, halogen or C.sub.1-4 alkoxy;X is oxygen; NR.sup.3 in which R.sup.3 is hydrogen, C.sub.1-4 alkyl, or -Y-R.sup.2 ; --C.dbd.O; or --CHOH;Y is --CH.sub.2 --CHOH, and when X is --C.dbd.O it may also be --CH.dbd.CH--; andR.sup.2 is C.sub.1-4 alkyl, one carbon atom of which is di- or tri-halogenated;or salts thereof, are useful in promoting growth of ruminants. Processes for their production, veterinary formulations and treatments are described.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: June 8, 1982
    Assignee: Beecham Group Limited
    Inventor: Brian G. McDonald
  • Patent number: 4327025
    Abstract: A process for the preparation of a styrylcyclopropane-1-carboxylic acid ester of the formula ##STR1## in which R is C.sub.1-4 -alkyl or an alcohol radical customary in pyrethroids,R.sup.1 is alkoxy or alkylthio, either of which may be optionally substituted by halogen,R.sup.2 is hydrogen or alkoxy, orR.sup.1 and R.sup.2 together are optionally halogen-substituted alkylenedioxy, andR.sup.3 is hydrogen or chlorine,comprising reacting an ester of the formula ##STR2## in which Hal is chlorine or bromine,with a base.The compounds are insecticidally active. Numerous syntheses of the starting materials, some involving new intermediates, are also shown.
    Type: Grant
    Filed: April 7, 1980
    Date of Patent: April 27, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Jautelat, Dieter Arlt, Reinhard Lantzsch, Rainer Fuchs, Hans-Jochem Riebel, Rolf Schroder, Horst Harnisch
  • Patent number: 4326055
    Abstract: This invention is directed to 5,6,7,8-tetrahydro-naphthyl or indanyl stilbene derivatives which are useful as tumor inhibiting agents, in the treatment of neoplasms, dermatological conditions and rheumatic illnesses.
    Type: Grant
    Filed: December 15, 1978
    Date of Patent: April 20, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Peter Loeliger
  • Patent number: 4322563
    Abstract: Substituted biphenyl-2-carboxaldehydes are prepared in good yield by reacting palladium complexes of substituted benzaldehyde aniline Schiff bases with substituted phenylmagnesium bromides in the presence of at least six, preferably eight, molar equivalents of triphenylphosphine.
    Type: Grant
    Filed: February 11, 1981
    Date of Patent: March 30, 1982
    Assignee: Merck & Co., Inc.
    Inventor: William F. Hoffman
  • Patent number: 4319048
    Abstract: Novel 9-phenyl 5,6-dimethyl-nona-2,4,6,8-tetraenoic acid, tetraenal or tetraenol derivatives useful as anti-tumor agents.
    Type: Grant
    Filed: July 30, 1980
    Date of Patent: March 9, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
  • Patent number: 4317933
    Abstract: This invention comprises an alkylation, reduction and transesterification process for the preparation of ester substituted phenols. The products are useful as antioxidants and may be prepared in high yields and with a high degree of purity.
    Type: Grant
    Filed: November 9, 1977
    Date of Patent: March 2, 1982
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Dane K. Parker
  • Patent number: 4309349
    Abstract: The process depicted, for example, by the formulae ##STR1## yields valuable intermediates in the manufacture of drugs.
    Type: Grant
    Filed: October 1, 1980
    Date of Patent: January 5, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Heinz W. Gschwend, Charles F. Huebner
  • Patent number: 4306097
    Abstract: Cycloalkanones, cycloalkanols and unsaturated analogs thereof, each of which has at the 3-position a 2-hydroxy-4-substituted phenyl group wherein the 4-position substituent is alkyl which can have an oxygen atom as part of the chain, or aralkyl which can have an oxygen atom as part of the alkyl chain, their use for pharmacological and medicinal purposes, intermediates therefor and processes for their preparation.
    Type: Grant
    Filed: September 8, 1980
    Date of Patent: December 15, 1981
    Assignee: Pfizer Inc.
    Inventors: Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4301081
    Abstract: The invention includes novel alkali metal complex compounds (and processes for their preparation) which are useful, inter alia for the hydrogenation of alkali metals at room temperature or below room temperature to form hydrides or nitrides.
    Type: Grant
    Filed: January 28, 1980
    Date of Patent: November 17, 1981
    Assignee: Studiengesellschaft Kohle mbH
    Inventor: Borislav Bogdanovic
  • Patent number: 4297520
    Abstract: p-Methoxytoluene is oxidized with a dichromate ion forming substance and sulfuric acid to give anisaldehyde in good yields. The oxidation proceeds with improved efficiency in the presence of a manganese compound.
    Type: Grant
    Filed: March 4, 1980
    Date of Patent: October 27, 1981
    Assignee: Daiwa Chemical Company Ltd.
    Inventor: Kozo Nakaoji
  • Patent number: 4296042
    Abstract: This process relates to the synthesis of unsaturated aliphatic esters useful as insect sex attractants, including gossyplure, the insect sex pheromone of the pink bollworm moth, Pectinophora gossypiella, and intermediates therefor. The process utilizes a cyclic phosphonium (Wittig) reagent.
    Type: Grant
    Filed: June 18, 1980
    Date of Patent: October 20, 1981
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, Michael C. Venuti
  • Patent number: 4290974
    Abstract: The invention relates to oxybenzylidenebornanones which correspond to the general formula: ##STR1## in which Z and Z' denote hydrogen or a radical SO.sub.3 H, at least one of the two radicals Z and Z' denoting hydrogen, R.sub.1 denotes hydrogen, an alkyl radical having 2 to 18 carbon atoms, an alkenyl radical having 3 to 18 carbon atoms, a radical --(CH.sub.2 CH.sub.2 O).sub.n H, ##STR2## --(CH.sub.2).sub.m CO.sub.2 R, in which R denotes H or an alkyl radical, --(CH.sub.2).sub.3 SO.sub.3 H or a divalent radical --(CH.sub.2).sub.m or --CH.sub.2 --CHOH--CH.sub.2, m having the values 1 to 10, n having the values 1 to 20 and p having the values 1 to 6, and R.sub.3 and R.sub.4 representing hydrogen or an optionally branched or hydroxylic alkyl radical, or forming an aminoaliphatic heterocyclic ring with the nitrogen atom, R.sub.2 denotes a hydrogen atom, an alkoxy radical or a divalent radical --O-- bonded to the radical R.sub.1 if the latter is also divalent, and q denotes 1 or 2; if q has the value 2, R.sub.
    Type: Grant
    Filed: July 10, 1979
    Date of Patent: September 22, 1981
    Assignee: L'Oreal
    Inventors: Claude Bouillon, Charles Vayssie
  • Patent number: 4284587
    Abstract: A new radioenzymatic assay for catecholamines utilizing the catechol-O-methyl transferase transfer of a methyl group from a labeled methyl donor to the catecholamines followed by isolation of the O-methylated(.sup.3 H)catecholamine and the subsequent measurement of radioactivity.
    Type: Grant
    Filed: October 12, 1978
    Date of Patent: August 18, 1981
    Assignee: The Upjohn Company
    Inventors: Garland A. Johnson, Jacob D. Peuler
  • Patent number: 4281207
    Abstract: Disclosed herein are monomeric compounds having the formula (I): ##STR1## wherein: R, R.sup.1, R.sup.2 and R.sup.3 are independently hydrogen or alkyl having from 1 to 4 carbon atoms;R.sup.4 is arylene having 6 to 18 carbon atoms;m is an integer from 1 to 4; andn is an integer from 0 to 4.These monomers can be homopolymerized or copolymerized with one or more other polymerizable monomers, and can particularly be copolymerized with those monomers having substituents which are susceptible to attack or degradation by a base. The resulting crosslinkable polymers are useful in relief image materials, such as photoresists and lithographic plates.
    Type: Grant
    Filed: October 26, 1979
    Date of Patent: July 28, 1981
    Assignee: Eastman Kodak Company
    Inventor: John C. Wilson
  • Patent number: 4275241
    Abstract: A process for the preparation of a-phenoxy-benzaldehyde which comprises contacting the 3-phenoxy-benzyl alcohol of the formula ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and represent hydrogen or halogen with an aqueous solution of a dichromate in the presence of aqueous sulphuric acid at a temperature in the range of 50.degree. to 125.degree. C. The 3-phenoxy-benzaldehyde can be in a mixture of other organic compounds such as obtained by hydrolyzing a 3-phenoxy toluene chlorinated in the side chain at a temperature of 140.degree.-210.degree. C. under pressure.
    Type: Grant
    Filed: October 29, 1979
    Date of Patent: June 23, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Siegfried Bohm, Alfons Klein, Karlfried Wedemeyer
  • Patent number: 4267344
    Abstract: N-Substituted N-carboxyanhydrides of .alpha.-amino acids, useful in peptide syntheses, and peptide synthesis process using such compounds, are disclosed. The N-substituent is penta(lower alkoxy)benzyl, or optionally substituted 9-xanthyl, 9-thioxanthyl or 9-selenoxanthyl.
    Type: Grant
    Filed: November 20, 1978
    Date of Patent: May 12, 1981
    Assignee: Proteinkemisk Institut. tilknyttet Akademiet for de tekniske Videnskaber
    Inventors: John B. Halstrom, Karoly G. Kovacs
  • Patent number: 4267382
    Abstract: Novel 9-(halo-substituted phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraene derivatives useful as anti-tumor agents are disclosed.
    Type: Grant
    Filed: February 4, 1980
    Date of Patent: May 12, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
  • Patent number: 4266073
    Abstract: Compounds representd by the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are lower alkyl, R.sub.4 is lower alkoxy, R.sub.6 and R.sub.8 are methyl or trifluoro methyl, R.sub.9 is formyl, hydroxymethyl, alkoxymethyl, alkanoyloxymethyl, carboxyl, alkoxycarbonyl, lower alkenoxycarbonyl, lower alkynoxycarbonyl, carbamoyl, mono(lower alkyl)-carbamoyl, di(lower alkyl)carbamoyl or N-heterocyclylcarbonyl, R.sub.5, R.sub.7, R.sub.10, R.sub.11, R.sub.12 and R.sub.13 are hydrogen or fluorine with the proviso that at least one of R.sub.5, R.sub.7, R.sub.10, R.sub.11, R.sub.12 or R.sub.13 is fluorine or at least one of R.sub.6 or R.sub.8 is trifluoro methyl, or pharmaceutically acceptable salts thereof useful as antitumor agents are disclosed.
    Type: Grant
    Filed: November 21, 1979
    Date of Patent: May 5, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Ka-Kong Chan, Beverly A. Pawson
  • Patent number: 4263223
    Abstract: A chemical compound of the formula: ##STR1## wherein X is a halogen selected from bromine, chlorine, iodine and fluorine, and preferably bromine; Z is selected from the group constituted by --CHO, --CH.dbd.NOH, --C.tbd.N; n is an integer from 1 to 11; m.sub.1 and m.sub.2, identical or different, are integers from 1 to 4.
    Type: Grant
    Filed: April 20, 1977
    Date of Patent: April 21, 1981
    Assignee: Laboratoires Serobiologiques S.A.
    Inventor: Marc Pauly
  • Patent number: 4258207
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO, --C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.
    Type: Grant
    Filed: March 15, 1979
    Date of Patent: March 24, 1981
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman