Oxy Bonded Directly To Benzene Ring Patents (Class 568/337)
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Patent number: 4439418Abstract: A topical cosmetic preparation for the treatment of seborrhea containing an antiseborrheically effective amount of at least one compound having the formula ##STR1## wherein Ar represents a member selected from the group consisting of phenyl, phenyl substituted with at least one group selected from the group consisting of alkyl having from 1 to 4 carbon atoms, alkoxy having from 1 to 4 carbon atoms, hydroxy and halo, naphthyl and heteroaromatic radical having from 4 to 5 carbon atoms in the cycle, and R represents a member selected from the group consisting of hydrogen, alkyl having from 1 to 4 carbon atoms, alkanoyl having from 1 to 4 carbon atoms, aryl and arylcarbonyl, where aryl has the same meaning as Ar, as an antiseborrheic, and further containing conventional vehicles and additives. The invention also relates to the process for reducing sebaceous cell sebum production employing said topical cosmetic preparation.Type: GrantFiled: December 9, 1981Date of Patent: March 27, 1984Assignee: Henkel KGaAInventors: Hinrich Moller, Siegfried Wallat, Friedhelm Bartnik
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Patent number: 4427686Abstract: A compound of the formula (I): ##STR1## wherein R.sub.1 is hydrogen or C.sub.1-6 alkyl;R.sub.2, R.sub.3 and R.sub.4 are the same or different and are chosen from hydrogen, hydroxyl, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy and C.sub.1-4 alkanoyl;G is H or OH; andm and n are independently 1 to 3; with the proviso that when G is OH, one of m or n is 1; is useful in the prophylaxis and treatment of diseases whose symptoms are controlled by the mediators of the allergic response, for example asthma, hay fever, rhinitis and allergic eczema.Type: GrantFiled: December 8, 1981Date of Patent: January 24, 1984Assignee: Beecham Group LimitedInventors: Derek R. Buckle, Harry Smith
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Patent number: 4422955Abstract: The invention relates to a process for substituting for a halogen atom attached to the nuclear carbon atom of an aromatic ring, a substituent of the formula --O--R wherein R represents alkyl, alkenyl, alkynyl or benzyl, which process comprises reacting the halogen-substituted aromatic compound with an alcoholate of the formula M.sup.n+ [O--R].sub.n.sup..crclbar. wherein M is an alkali metal atom or alkaline earth metal atom, n is the valency of M, and R is as defined above, in the presence of an active catalyst mixture comprising (i) a formic acid ester of an organic alcohol having the formula R.sup.2 --O--CO--H wherein R.sup.2 is as defined for R above; and (ii) a cuprous salt; in a liquid medium which is a solvent for the catalyst mixture and in which the halogen-substituted aromatic compound is at least partially soluble, under substantially anhydrous conditions and a non-oxidizing atmosphere. The invention further relates to a catalyst used in the above process.Type: GrantFiled: December 4, 1981Date of Patent: December 27, 1983Assignee: Sterling Drug Inc.Inventor: Robert J. Bryant
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Patent number: 4410732Abstract: Ketone derivatives represented by the general formula (I) ##STR1## where R is --CH.sub.2 R.sup.1 (where R.sup.1 is a hydrogen atom or an alkyl group), a halogen-substituted alkyl group, a cyano-substituted alkyl group, a cyclopropyl group, ##STR2## (where R.sup.2 is a hydrogen atom or an alkyl group and Y is a hydrogen atom or a halogen atom) or ##STR3## (where R.sup.3 is a hydrogen atom, an alkyl group, a phenyl group or a halogen-substituted phenyl group, and Z is a hydrogen atom or a halogen atom), and X is an oxygen atom or a sulfur atom.Type: GrantFiled: June 14, 1982Date of Patent: October 18, 1983Assignee: Nissan Chemical Industries Ltd.Inventors: Kiyomi Ozawa, Yasuyuki Nakajima, Makoto Tsugeno
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Patent number: 4407757Abstract: Novel compounds of the formulae ##STR1## wherein R represents lower alkyl or lower alkoxy, A represents --CH.sub.2 --, --CO-- or ##STR2## n represents an integer of 1 to 8, X represents hydrogen or hydroxyl which may be protected and Y represents hydroxyl which may be protected, and their esters show an excellent action on the lysosomal membranes of cells, and exhibit excellent pharmacological activities such as physiologic host defense control activity, especially immuno-potentiating activity.Type: GrantFiled: December 31, 1980Date of Patent: October 4, 1983Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroshi Morimoto, Isuke Imada, Masazumi Watanabe, Mitsuru Kawada
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Patent number: 4400542Abstract: There is described a process for the production of a 4,6-diacetyl resorcinol having an alkyl C 1 to 6 or an alkenyl C 2 to 6 group in the 2-position, which comprises reacting 4,6-diacetyl resorcinol with an alkyl C 1 to 6- or an alkenyl C 2 to 6- halide.The product 4,6-diacetyl resorcinols are useful as intermediates in the production of pharmaceuticals. Certain of the product 4,6-diacetyl resorcinols are novel.Type: GrantFiled: April 22, 1981Date of Patent: August 23, 1983Assignee: Fisons LimitedInventors: David K. Rainey, Michael M. Fanthorpe
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Patent number: 4371708Abstract: 4-substituted 3,3-dimethyl-butan-2-ones of the formula ##STR1## in which R represents cyano or the grouping --X--R.sup.1,whereinR.sup.1 represents n-alkyl with 1 to 4 carbon atoms, isopropyl, isobutyl, sec.-butyl, alkenyl with 3 to 4 carbon atoms, alkynyl with 3 to 4 carbon atoms, optionally substituted aryl or substituted aralkyl, or represents cyano provided that X represents --O-- or --S--, andX represents --O--, --S--, --SO--, or --SO.sub.2 --,which are intermediates for the synthesis of fungicides.Type: GrantFiled: May 20, 1981Date of Patent: February 1, 1983Assignee: Bayer AktiengesellschaftInventors: Wolfgang Kramer, Hans-Ludwig Elbe
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Patent number: 4350833Abstract: 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: GrantFiled: January 28, 1981Date of Patent: September 21, 1982Inventor: Kunihiro Ichimura
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Patent number: 4331597Abstract: Penicillin compounds and methods for the production thereof are described, said penicillin compounds being represented by the formula (I) ##STR1## wherein R.sub.1, R.sub.2, and R.sub.3 each represents hydrogen, a lower alkyl group, a halogen atom, a lower alkoxy group, a hydroxyl group, or a substituted or unsubstituted phenylalkoxy group except that R.sub.1, R.sub.2, and R.sub.3 cannot all represent hydrogen simultaneously; R.sub.4 represents hydrogen or a lower alkyl group; and R.sub.5 represents hydrogen or a hydroxyl group.Type: GrantFiled: October 2, 1980Date of Patent: May 25, 1982Assignee: Meiji Seika Kaisha, Ltd.Inventors: Osamu Makabe, Yasushi Murai, Tuneo Okonogi, Masahiro Onodera, Takashi Yoshida, Shunzo Fukatsu
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Patent number: 4316042Abstract: Compounds of the formula II: ##STR1## are produced by reacting a compound of the formula III ##STR2## with a compound of the formula IV: ##STR3## wherein R.sub.1 is hydrogen, alkyl of 1 to 5 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by cycloalkyl of 3 to 6 carbon atoms, polyhaloalkyl of 1 to 5 carbon atoms, allyl, propargyl, enzyl or aryl,R.sub.2 is hydrogen, halogen, alkyl or alkoxy, each of 1 to 4 carbon atoms, trifluoromethyl, nitro, alkylamino or dialkylamino, wherein the alkyl groups have 1 to 4 carbon atoms, or aryl,R.sub.3 is hydrogen, halogen, alkyl or alkoxy, each of 1 to 4 carbon atoms, or aryl,R.sub.4 is hydrogen, nitro, halogen, alkyl or alkoxy each of 1 to 4 carbon atoms or aryl,R.sub.5 is hydrogen, halogen, alkyl, alkylthio or alkoxy each of 1 to 4 carbon atoms, nitro, trifluoromethyl or aryl,R.sub.6 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, benzyl or aryl, andR is alkyl of 1 to 4 carbon atoms.Type: GrantFiled: August 15, 1979Date of Patent: February 16, 1982Assignee: Sandoz Ltd.Inventor: Peter Funfschilling
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Patent number: 4301166Abstract: The invention relates to hydroxyethyl-azole compounds and methods for their preparation. Also included in the invention are compositions containing said hydroxyethyl-azole compounds and methods for the use of said compounds and compositions as antimycotic agents.Type: GrantFiled: November 9, 1979Date of Patent: November 17, 1981Assignee: Bayer AktiengesellschaftInventors: Erik Regel, Karl H. Buchel, Ingo Haller, Manfred Plempel
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Patent number: 4291061Abstract: 2,3-Dichloro-7-hydroxy-1H-inden-1-one derivatives of the formula I ##STR1## wherein R.sub.1 is hydrogen or one of the groups ##STR2## R.sub.2 and R.sub.3 independently of one another are each hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, trifluoromethyl or nitro,R.sub.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.4 -alkenyl, each of which is unsubstituted or substituted by halogen, or R.sub.4 is phenyl which is unsubstituted or is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, trifluoromethyl, cyano or nitro, or it is a C.sub.3 -C.sub.6 -cycloalkyl group, andR.sub.5 is C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl or C.sub.2 -C.sub.4 -alkenyl.These compounds exhibit a microbicidal action against in particular phytopathogenic fungi and bacteria.Type: GrantFiled: October 31, 1979Date of Patent: September 22, 1981Assignee: Ciba-Geigy CorporationInventors: Elmar Sturm, Robert Nyfeler
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Patent number: 4289495Abstract: Oxidative dye compositions for keratin fibres are provided which contain a 2,5-dihydroxyphenylalkanoic acid or salt thereof as antioxidant.Type: GrantFiled: August 18, 1978Date of Patent: September 15, 1981Assignee: L'OrealInventors: Andree Bugaut, Jean-Francois Grollier, Jean-Jacques Vandenboosche
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Patent number: 4286091Abstract: Valuable pyridazinone intermediates to pharmaceutically useful compounds can be prepared in surprisingly high yields by the reaction of the corresponding monohydrazone with diketene, preferably in the presence of a basic catalyst. In an especially preferred embodiment, p,p'-dichlorobenzil monohydrazone and diketene are reacted in a xylene solvent in the presence of triethylamine to afford 4-acetyl-5,6-bis(p-chlorophenyl)-2H-pyridazin-3-one, which can then be reacted with ethylene carbonate in the presence of potassium carbonate to afford the antihypertensive agent, 4-acetyl-5,6-bis(p-chlorophenyl)-2-(2'-hydroxyethyl)-2H-pyridazine-3-one.Type: GrantFiled: May 19, 1980Date of Patent: August 25, 1981Assignee: Diamond Shamrock CorporationInventors: Russell M. Bimber, Russell Buchman, Michael F. DePompei, Larry J. Powers
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Patent number: 4275071Abstract: Imidazole derivatives of the formula I and pharmaceutically acceptable acid addition salts thereof are provided: ##STR1## In the formula, R.sub.4 1- or 2-naphthyl, optionally substituted with Cl, Br, or I; 1,2,3,4-tetrahydro-6-naphthyl; 3-duryl, optionally 6-substituted by Cl, Br, I, NO.sub.2, CH.sub.3 or benzyl; mesityl, phenyl 2-, 3- or 4-substituted by OH, NH.sub.2, NO.sub.2, CH.sub.3 CONH, phenyl, phenoxy, cyclohexyl, phenylthio, benzylthio, C.sub.1 -C.sub.6 alkyl or C.sub.1 C.sub.6 alkylthio; 4-bibenzylyl; 3,4-dihydroxyphenyl,n=0, 1 or 2 and(a) R=H, alkyl having 1 to 6 carbon atoms or phenyl R.sub.1 =H, alkyl having 1 to 6 carbon atoms or phenyl one of R.sub.2 and R.sub.3 =H the other of R.sub.2 and R.sub.3 =H, OH, benzoyloxy, C.sub.2 -C.sub.7 alkanoyloxy, N-(C.sub.1 -C.sub.6 alkyl)-carbamoyloxy, N,N-[di-(C.sub.1 C.sub.6)alkyl]-carbamoyloxy, but if R.sub.2 =R.sub.3 =H then R=R.sub.1 =H, or(b) R=H, C.sub.1 -C.sub.6 alkyl, phenyl R.sub.1 =H, C.sub.1 -C.sub.6 alkyl, phenyl R.sub.2 +R.sub.Type: GrantFiled: July 10, 1979Date of Patent: June 23, 1981Assignee: Recordati S.A.Inventors: Dante Nardi, Alberto Tajano, Maria J. Magistretti
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Patent number: 4229470Abstract: Compounds are disclosed which have a juvenile hormone action on insects and also exhibit acaricide action. Said compounds are unsaturated aliphatic compounds having a trichloromethyl end group and the other end group of which is a phenol group which may be substituted and/or condensed, and which are capable of hindering the growth of insects from the larval to the adult stage and also exhibit an acaricide action on both adult acari and their eggs.Type: GrantFiled: January 17, 1979Date of Patent: October 21, 1980Assignee: Montedison S.p.A.Inventors: Paolo Piccardi, Angelo Longoni
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Patent number: 4225619Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is perfluoroalkyl of 1 to 8 carbon atoms or 2,2,3,3-tetrafluoro-cyclobutyl,R.sub.2 and R.sub.4, which may be identical to or different from each other, are each hydrogen, alkyl of 1 to 10 carbon atoms, aliphatic acyl of 2 to 18 carbon atoms, benzoyl, salicyloyl or phenylacetyl, andR.sub.3 and R.sub.5, which may be identical to or different from each other, are each alkyl of 3 to 18 carbon atoms, halogen, nitro, p-toluenesulfonyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclododecyl, methylcyclohexyl, dimethylcyclohexyl, benzyl, methylthio or ##STR2## where R.sub.1, R.sub.2 and R.sub.4 have the meanings previously defined,Q is --CH.sub.2 -- or --S--, andG is R.sub.5, as above defined, orQ is R.sub.3, as above defined, andG is --CH.sub.2 -- or --S--,R.sub.3 may, in addition, also be hydroxyl, methoxy, methyl or cyano, andR.sub.5 may also be methyl, orone of substituents R.sub.3 and R.sub.Type: GrantFiled: March 19, 1979Date of Patent: September 30, 1980Assignee: Boehringer Ingelheim GmBHInventors: Rolf Brickl, Hans Eberhardt, Karl-Richard Appel, Uwe Lechner, Walter Merk
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Patent number: 4209621Abstract: This disclosure describes substituted 1,2,4-triazolo[1,5-a]pyrimidines and substituted 1,2,4-triazolo[4,3-a]pyrimidines which possess anxiolytic activity.Type: GrantFiled: April 27, 1979Date of Patent: June 24, 1980Assignee: American Cyanamid CompanyInventors: John P. Dusza, Robert A. Hardy, Jr., Jay D. Albright
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Patent number: 4202840Abstract: Compounds having the following structural formula ##STR1## wherein R is alkyl which are useful as herbicides.Type: GrantFiled: September 29, 1978Date of Patent: May 13, 1980Assignee: Stauffer Chemical CompanyInventors: Reed A. Gray, Chien K. Tseng, Ronald J. Rusay
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Patent number: RE30377Abstract: 8-Methoxypsoralen is prepared in six steps from pyrogallol including condensation of pyrogallol with a two-fold excess of chloroacetic acid with boron trifluoride hydrogenation of .[.6,7-dihydroxy-2,3-dihydrobenzofuran.]. .Iadd.6,7-dihydroxycoumaranone .Iaddend.and dehydrogenation of .[.2,3.]. .Iadd.4',5'.Iaddend.-dihydroxanthotoxin. Improvements in these three steps lead to a marked overall increase in yield.Type: GrantFiled: August 20, 1979Date of Patent: August 19, 1980Assignee: Thomas C. Elder, Inc.Inventors: Louis J. Glunz, Donald E. Dickson