Benzene Ring Bonded Directly Or Attached Indirectly By An Acyclic Carbon Or An Acyclic Carbon Chain To Ring Carbon Of The Five-membered Hetero Ring Patents (Class 548/511)
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Patent number: 5210214Abstract: A process for preparing indolenines of the formula I ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are independently of one another hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.3 -C.sub.8 -cycloalkyl, aryl, C.sub.7 -C.sub.20 -alkylphenyl, C.sub.7 -C.sub.20 -phenalkyl, or R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3 together are an unsubstituted or C.sub.1 -C.sub.12 -alkyl-substituted C.sub.3 -C.sub.8 -alkylene chain,X and Y are independently of one another hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.2 -C.sub.8 -alkoxyalkyl, C.sub.2 -C.sub.8 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkylsulfonyl, halogen, nitro or cyano,by reacting a 4-methylene-1,3-dioxolan-2-one of the formula II ##STR2## where R.sup.1, R.sup.2 and R.sup.3 are each as defined above, with an aniline of the formula III ##STR3## where X and Y are each as defined above, in the presence of a Lewis acid and in the presence or absence of a halide of main group 1 or 2 of the Periodic Table at from 100.degree.Type: GrantFiled: April 10, 1992Date of Patent: May 11, 1993Assignee: BASF AktiengesellschaftInventors: Klaus Diehl, Martin Fischer, Manfred Dimmler
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Patent number: 5185361Abstract: A pharmaceutical compound of the formula ##STR1## in which A is selected from --NHCOR.sup.1, --NHCOOR.sup.1, --NHCONHR.sup.1, --NHCSNHR.sup.1, --CONHR.sup.1, where R.sup.1 is optionally halo-substituted C.sub.1-10 alkyl, C.sub.2-10 alkenyl, C.sub.3-7 cycloalkyl-C.sub.1-4 alkyl or phenyl-C.sub.1-4 alkyl B is optionally substituted phenyl, and --X--Y-- is --CH=CH-- or --CH.sub.2 --CH.sub.2 --; and salts thereof. The compounds are leukotriene antagonists.Type: GrantFiled: September 18, 1991Date of Patent: February 9, 1993Assignee: Lilly Industries LimitedInventor: Jeremy Gilmore
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Patent number: 5183894Abstract: The present invention relates to 2-substituted-1-hydroxyindoles of the following formula: ##STR1## wherein, R.sup.1 is an electron withdrawing group,R.sup.2 is an alkenyl having 2-10 carbon atoms, and N-substituted .alpha.-iminobenzyl group wherein the substituents are selected from the group consisting of phenyl, anilino and dimethylamino, an unsubstituted aromatic group, and an aromatic group having meta or para substituents which are nitro, trifluoromethyl, fluoro, formyl, hydroxyiminomethyl and carbamoyl,R.sup.3 is a halogen atom, andn is 0, 1, or 2,provided that when R.sup.2 is either phenyl or nitro substituted phenyl and n is 0, then R.sup.1 is not cyano.Type: GrantFiled: July 1, 1991Date of Patent: February 2, 1993Assignee: Eastman Kodak CompanyInventors: William R. Schleigh, Thomas R. Welter
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Patent number: 5149819Abstract: Squarylium compounds having the following formula (I), ##STR1## and an optical information recording medium comprising a substrate, and a recording layer formed on the substrate, comprising a squarylium compound having formula (II) are disclosed: ##STR2##Type: GrantFiled: May 1, 1991Date of Patent: September 22, 1992Assignees: Ricoh Company, Ltd., Kyowa Hakko Kogyo Co., Ltd.Inventors: Tsutomu Satoh, Ikuo Shimizu, Yukiyoshi Ito
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Patent number: 5118695Abstract: 1-Hydroxyindoles of the following formula are useful in controlling fungi: ##STR1## wherein: R.sup.1 is hydrogen or an electron withdrawing group;R.sup.2 is selected from the group consisting of alkenyl having 2-10 carbon atoms, N-substituted-.alpha.-iminobenzyl, an unsubstituted or substituted aromatic group and acyl of 2-16 carbon atoms,R.sup.3 is selected from the group consisting of halogen atoms, andn is 0 to 4.Type: GrantFiled: August 6, 1990Date of Patent: June 2, 1992Assignee: Eastman Kodak CompanyInventors: William R. Schleigh, Thomas R. Welter
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Patent number: 5106990Abstract: The present invention relates to a dye represented by formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6, which may be the same or different, each represents a C.sub.1 -C.sub.5 alkyl group or a C.sub.1 -C.sub.5 alkyl group having a substituent selected from the group consisting of a sulfonic group, carboxyl group and hydroxyl group, and Z.sup.1 and Z.sup.2 each represents a group of non-metallic atoms necessary for the formation of a benzo-condensed of naphtho-condensed ring, or a benzo-condensed or naphtho-condensed ring having a substituent selected from the group consisting of a sulfonic group, a carboxyl group, an hydroxyl group, a halogen atom, a cyano group, an amino group and a C.sub.1 -C.sub.5 alkyl group connected to the ring directly or through a divalent connection group, with a proviso that R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, Z.sup.1 and Z.sup.Type: GrantFiled: March 28, 1989Date of Patent: April 21, 1992Assignee: Fuji Photo Film Co., Ltd.Inventors: Shigeru Ohno, Yuji Mihara, Keiichi Adachi
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Patent number: 5097034Abstract: Color formers of the formula ##STR1## in which X.sup.1 denotes hydroxyl, alkoxy, alkenyloxy, aralkoxy, cycloalkoxy, aryloxy or acyloxy,R.sup.1 denotes hydrogen, halogen, alkyl or alkoxy,R.sup.2 denotes hydrogen, alkoxy, aralkoxy, aryloxy or a radical of the formula ##STR2## Y.sup.1 and Y.sup.2, independently of one another, denote alkyl, cycloalkyl or aralkyl,R.sup.2 can form a heterocyclic ring with A in the o-position, in which a benzene ring can be additionally fused onto ring A in the o-/m-position with respect to R.sup.2,R.sup.3 denotes hydrogen, alkyl, alkenyl, aralkyl, cycloalkyl or aryl, or R.sup.3 is linked to ring B in the o-position with respect to the nitrogen,Z.sup.1 stands for the remaining members of a partially hydrogenated or completely hydrogenated ring, with the proviso that Z.sup.Type: GrantFiled: May 14, 1991Date of Patent: March 17, 1992Assignee: Bayer AktiengesellschaftInventor: Udo Eckstein
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Patent number: 5041460Abstract: This invention provides a series of novel heter-aliphatic carboxamides of formula I in which the group >Z--Y--X< is selected from >C.dbd.CH--N<, >N--CH.dbd.C<, >C.dbd.N--N< and >N--N.dbd.C< and the other radicals have the meanings defined in the following specification. The compounds of formula I are leukotriene antagonists. The invention also provides pharmaceutically acceptable salts of the formula I compounds; pharmaceutical compositions containing the formula I compound, or their salts, for use in the treatment of, for example, allergic or inflammatory diseases, or endotoxic or traumatic shock conditions; and processes for the manufacture of the formula I compounds, as well as intermediates for use in such manufacture.Type: GrantFiled: April 12, 1989Date of Patent: August 20, 1991Assignee: ICI Americas Inc.Inventor: Victor G. Matassa
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Patent number: 5001294Abstract: Aromatic alkenes, especially diarylbutadienes are produced in a simple economic process by reaction of an anil with an organic compound having a non-aromatic unsaturated system conjugated with an aromatic system, and a terminal methyl group pendent from the non-aromatic unsaturated system; in particular the organic compound is a propenyl-substituted aromatic compound.Type: GrantFiled: October 31, 1988Date of Patent: March 19, 1991Inventor: Allan S. Hay
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Patent number: 4990669Abstract: The invention relates to new optically active .alpha.-amino aldehydes of the formulae ##STR1## in which R.sub.1 represents an optionally substituted alkyl, alkenyl, aralkyl or aryl radical, andR.sub.2 and R.sub.3, independently of one another, denote an optionally substituted alkyl, alkenyl, cycloalkyl or aralkyl group, together form an optionally substituted phenylene-(1,2)-bis-methylene radical, or R.sub.2 is an optionally substituted, alkyl, cycloalkyl or aralkyl radical, and R.sub.3 forms together with R.sub.1 a 1,3-propylene radical.a process for the preparation thereof, and the use thereof for the stereoselective preparation of optically active .beta.-amino alcohols.Type: GrantFiled: March 23, 1988Date of Patent: February 5, 1991Assignee: Bayer AktiengesellschaftInventors: Manfred T. Reetz, Mark W. Drewes
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Patent number: 4977272Abstract: This invention relates to new compounds of the formula: ##STR1## where each of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 has zero to 10 C atoms, and no acetylenic unsaturation; each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 is independently selected from H and hydrocarbyl; with the proviso that R.sup.6 is C.sub.1 -C.sub.10 hydrocarbyl; each of R.sup.5 and R.sup.Type: GrantFiled: June 29, 1989Date of Patent: December 11, 1990Assignee: The Standard Oil CompanyInventors: Mark C. Cesa, James E. Rinz, Gilles Klopman, Teodora T. Kopp
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Patent number: 4943572Abstract: Aminoalkylindoles of the formula ##STR1## and 1-carbamoylalkyl-2-phenlindoles of the formula ##STR2## exhibit substantial estrogenic activity and a relatively low degree of anti-estrogenic activity.Type: GrantFiled: June 23, 1989Date of Patent: July 24, 1990Assignee: Schering AktiengesellschaftInventor: Erwin von Angerer
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Patent number: 4914213Abstract: A 5-hydroxy-N-substituted indole derivative and the process for producing the indole derivative are described the indole derivative is produced by a process comprising reacting a phenol derivative having an unsaturated double bond in the m-position with a diazonium salt.Type: GrantFiled: February 4, 1987Date of Patent: April 3, 1990Assignee: Fuji Photo Film Co., Ltd.Inventor: Masato Satomura
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Patent number: 4910216Abstract: A compound of the formula ##STR1## wherein R.sub.1 is a hydrogen atom or a methoxy group, and A is a C.sub.1 -C.sub.4 alkylene group, or a pharmaceutically acceptable salt thereof. This compound is useful as a medicine, particularly as a lipoxygenase inhibitor for polyunsaturated fatty acids.Type: GrantFiled: February 25, 1988Date of Patent: March 20, 1990Assignee: Teikoku Hormone Mfg. Co., Ltd.Inventors: Yasushi Suzuki, Yukio Hasegawa, Michitaka Sato, Morinobu Saito, Norio Yamamoto, Katsuhiko Miyasaka, Takashi Mikami, Katsuhiko Miyazawa
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Patent number: 4831156Abstract: The disclosure relates to compounds of the formula ##STR1## and pharmaceutically acceptable addition salts thereof wherein X represents a substituted or unsubstituted alkylene chain containing 1 to 4 carbon atoms, wherein R.sub.5 is a lower alkyl group, wherein R.sub.6 is either hydrogen or methyl, R.sub.9 is hydrogen or lower alkyl, wherein Am is selected from the class consisting of amino, lower mono and dialkylamino, piperidino, piperazino, N-lower alkyl piperazino, pyrrolidino, and morpholino groups, wherein Y.sub.1 and Y.sub.2 are identical and are hydrogen, halogen, methyl or ethyl and n is an integer in the range of 1-5.Type: GrantFiled: September 30, 1987Date of Patent: May 16, 1989Assignee: The University of Tennessee Research Corp.Inventors: Thomas P. Kennedy, George W. Kabalka
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Patent number: 4764616Abstract: The invention relates to benzopyrrolobenzodiazepines and quinobenzodiazepines of the formula ##STR1## where X and Y may be the same or different and each is hydrogen, halogen, CF.sub.3, lower alkyl, lower alkoxy, lower alkylthio and lower alkylsulfonyl, p and q are independently 1 or 2; R.sub.1 is hydrogen when R.sub.2 is bonded to R.sub.3 to form a --(CH.sub.2).sub.m --CH.sub.2 -- group or a --CH.dbd.CH-- group; R.sub.3 is hydrogen when R.sub.1 is bonded to R.sub.2 to form a --(CH.sub.2).sub.m --CH.sub.2 -- group or a --CH.dbd.CH-- group; m is 1 or 2; R.sub.4 is NR.sub.5 R.sub.6 wherein R.sub.5 is hydrogen or lower alkyl and R.sub.6 is hydrogen, lower alkyl or a group of the formula (CH.sub.2).sub.n NR.sub.7 R.sub.8 wherein R.sub.7 and R.sub.8 are lower alkyl, and n is 2 or 3, ##STR2## wherein R.sub.9 is lower alkyl, ##STR3## wherein R.sub.10 is CH.sub.2 CH.sub.2 OH, lower alkyl, phenyl, phenyl substituted by halogen, CF.sub.Type: GrantFiled: November 12, 1986Date of Patent: August 16, 1988Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Edward J. Glamkowski, Yulin Chiang
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Patent number: 4755610Abstract: New alkaloids called hapalindoles, which are antibacterial and antifungal agents, and methods of preparing these alkaloids by culturing the blue-green alga Hapalosiphon fontinalis ATCC 39694, are provided.Type: GrantFiled: February 14, 1986Date of Patent: July 5, 1988Assignee: University of HawaiiInventors: Richard E. Moore, Gregory M. L. Patterson
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Patent number: 4749701Abstract: Disclosed are an aminostyryl compound represented by Formula I: ##STR1## wherein A represents a linking group having 3 to 4 chain members; B represents an unsubstituted or substituted 5 to 6-membered monocyclic type heterocyclic residue containing 1 to 2 hetero atoms, an unsubstituted or substituted condensed heterocyclic residue which contains 5 to 6-membered monocyclic type heterocycle containing 1 to 2 hetero atoms, a naphthyl group or an alkyl group having 5 to 7 carbon atoms,a composition having leukotriene antagonism which contains an aminostyryl compound represented by Formula I as the effective ingredient, and a method of antagonizing SRS based on leukotriene antagonistic activity by employing the same.Type: GrantFiled: December 15, 1986Date of Patent: June 7, 1988Assignee: Mitsubishi Chemical Industries LimitedInventors: Yoshio Hayashi, Tomei Oguri, Masaki Shinoda, Kazuo Takahashi
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Patent number: 4740601Abstract: An imidazole derivative having antimicrobial activities against bacteria, fungi, yeast, pathogenic plant fungi and the like represented by the following general formula (I): ##STR1## wherein R.sub.1 means a hydrogen or halogen atom or a lower alkyl group, R.sub.2 denotes a hydrogen atom or an alkyl, alkenyl, haloalkyl or substituted or unsubstituted benzyl group, R.sub.3 stands for a hydrogen or halogen atom, and R.sub.4 is a substituted or unsubstituted benzylthio group, a phenylthio, alkylthio, alkenylthio, furfurylthio, alkoxy or phenoxy group or a halogen atom; or an acid addition salt thereof.Type: GrantFiled: December 15, 1986Date of Patent: April 26, 1988Assignee: SS Pharmaceutical Co., Ltd.Inventors: Masaki Ogawa, Hideaki Matsuda, Takemitsu Asaoka, Junji Oono, Tatsuhiko Katori
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Patent number: 4723007Abstract: The invention relates to benzopyrrolobenzodiazepines and quinobenzodiazepines of the formula ##STR1## where X and Y may be the same or different and each is hydrogen, halogen, CF.sub.3, lower alkyl, lower alkoxy, lower alkylthio and lower alkylsulfonyl, p and q are independently 1 or 2; R.sub.1 is hydrogen when R.sub.2 is bonded to R.sub.3 to form a --(CH.sub.2).sub.m --CH.sub.2 -- group or a --CH.dbd.CH-- group; R.sub.3 is hydrogen when R.sub.1 is bonded to R.sub.2 to form a --(CH.sub.2).sub.m --CH.sub.2 -- group or a --CH.dbd.CH-- group; m is 1 or 2; R.sub.4 is NR.sub.5 R.sub.6 wherein R.sub.5 is hydrogen or lower alkyl and R.sub.6 is hydrogen, lower alkyl or a group of the formula (CH.sub.2).sub.n NR.sub.7 R.sub.8 wherein R.sub.7 and R.sub.8 are lower alkyl, and n is 2 or 3, ##STR2## wherein R.sub.9 is lower alkyl, ##STR3## wherein R.sub.10 is CH.sub.2 CH.sub.2 OH, lower alkyl, phenyl, phenyl substituted by halogen, CF.sub.Type: GrantFiled: November 12, 1986Date of Patent: February 2, 1988Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Edward J. Glamkowski, Yulin Chiang
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Patent number: 4697018Abstract: The invention provides processes for the preparation of both known and novel [bis(substituted-aryl) (indolyl)]methanes and [(substituted-aryl) (heteryl) (indolyl)]methanes, useful as color formers, particularly in carbonless duplicating and thermal marking systems, which comprises the interaction of [bis(substituted-aryl) (phenylsulfonyl)]methanes and [(substituted-aryl) (heteryl) (phenylsulfonyl)]methanes with indoles in the presence of either an alkaline or an acidic catalyst.Type: GrantFiled: September 30, 1985Date of Patent: September 29, 1987Assignee: The Hilton-Davis Chemical Co.Inventors: Paul J. Schmidt, William M. Hung
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Patent number: 4695581Abstract: A compound represented by the formula ##STR1## wherein R.sub.1 represents a lower alkyl group; each of R.sub.2 and R.sub.3 represents an alkyl group having 1 to 3 carbon atoms; and each of R.sub.4, R.sub.5 and R.sub.6 represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkanoyloxy group, an aralkyloxy group, a lower alkylthio group, a lower haloalkyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, a mono- or di-(lower alkyl or aralkyl)amino group or a group of the formula ##STR2## in which R.sub.7 represents a lower alkylene group having at least 2 carbon atoms, one of R.sub.8 and R.sub.9 represents a hydrogen atom or a lower alkyl group and the other represents a lower alkyl group, and R.sub.10 represents a hydrogen atom or a lower alkyl group; or any two of R.sub.4, R.sub.5 and R.sub.6 which are adjacent to each other, together, represent a lower alkylenedioxy group, and a salt thereof; and a process for production thereof.Type: GrantFiled: August 29, 1985Date of Patent: September 22, 1987Assignee: Teikoku Hormone Mfg. Co., Ltd.Inventors: Yasushi Suzuki, Yukio Hasegawa, Michitaka Sato, Morinobu Saito, Norio Yamamoto, Katsuhiko Miyasaka, Takashi Mikami, Katsuhiko Miyazawa
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Patent number: 4661511Abstract: Pharmaceutical compositions are provided containing a 2-(hydroxyphenyl)-indole or a 2-(C.sub.2 -C.sub.6 -alkanoxyloxyphenyl) indole and a pharmaceutically acceptable carrier.Type: GrantFiled: July 27, 1984Date of Patent: April 28, 1987Assignee: Degussa AktiengesellschaftInventors: Erwin von Angerer, Helmut Schonenberger
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Patent number: 4558137Abstract: The invention provides processes for the preparation of both known and novel [bis(substituted-aryl) (indolyl)]methanes and [(substituted-aryl) (heteryl) (indolyl)]methanes, useful as color formers, particularly in carbonless duplicating and thermal marking systems, which comprises the interaction of [bis(substituted-aryl) (phenylsulfonyl)]methanes and [(substituted-aryl) (heteryl) (phenylsulfonyl)]methanes with indoles in the presence of either an alkaline or an acidic catalyst.Type: GrantFiled: June 6, 1983Date of Patent: December 10, 1985Assignee: The Hilton-Davis Chemical Co.Inventors: Paul J. Schmidt, William M. Hung
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Patent number: 4543360Abstract: Pharmaceutical compositions are provided containing a 2-(hydroxyphenyl)-indole or a 2-(C.sub.2 -C.sub.6 -alkanoyloxyphenyl) indole and a pharmaceutically acceptable carrier.Type: GrantFiled: August 17, 1982Date of Patent: September 24, 1985Assignee: Degussa AktiengesellschaftInventors: Erwin von Angerer, Helmut Schonenberger
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Patent number: 4542223Abstract: Methine dyestuffs of the formula ##STR1## are prepared by subjecting a compound ##STR2## to a condensation reaction with a compoundA--CHO (VI)and with 1 to 5 equivalents of an inorganic acid in the presence of 0-30% by weight of an organic solvent and 0-15% by weight of water.Type: GrantFiled: March 14, 1983Date of Patent: September 17, 1985Assignee: Bayer AktiengesellschaftInventors: Roderich Raue, Hans-Peter Kuhlthau, Klaus-Friedrich Lehment
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Patent number: 4542224Abstract: Cationic methine dyestuffs of the formula ##STR1##Type: GrantFiled: April 4, 1983Date of Patent: September 17, 1985Assignee: Bayer AktiengesellschaftInventors: Roderich Raue, Hans-Peter Kuhlthau
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Patent number: 4510158Abstract: 4-(1-R'-2-phenyl-1H-indol-3-yl)-3-cyclohexene-1-carboxylic acids, 4-(1'R'-2-phenyl-1H-indol-3-yl)cyclohexane-1-carboxylic acids, 4-(1-R'-2-phenyl-1H-indol-3-yl)benzoic acids, the corresponding cyclohexene- and cyclohexane-1,1-dicarboxylic acids, and lower-alkyl esters thereof, wherein R' is hydrogen or lower-alkyl, are prepared by reacting a 1-R'-2-phenyl-1H-indole with a cyclohexanone-4-carboxylic acid or -4,4-dicarboxylic acid, followed as desired by a hydrogenation or aromatization process. The compounds which are free carboxylic acids or salts thereof are useful as complement inhibitors. The corresponding esters are useful as intermediates.Type: GrantFiled: March 5, 1984Date of Patent: April 9, 1985Assignee: Sterling Drug Inc.Inventor: Denis M. Bailey
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Patent number: 4454158Abstract: Compounds of the formula ##STR1## wherein: R is phenyl, phenyl monosubstituted, disubstituted, or trisubstituted by (C.sub.1 -C.sub.8) alkyl, (C.sub.1 -C.sub.8)alkoxy, hydroxy, chlorine, bromine, iodine, fluorine, trifluoromethyl, nitro, (C.sub.1 -C.sub.6)alkylcarbonyl, benzoyl, or phenyl; 1-, or 2-naphthyl; 1-, 2-, or 3-indenyl; 1-, 2-, or 9-fluorenyl; 1-, 2-, or 3-piperidinyl; 2- or 3-pyrrolyl; 2- or 3-thienyl; 2- or 3-furanyl; 2- or 3- indolyl; 2- or 3-thianaphthenyl; or 2- or 3-benzofuranyl;R.sub.1 is hydrogen, (C.sub.1 -C.sub.8)alkyl, benzyl, or phenethyl;X and Y independently, are hydrogen, fluorine, chlorine, or bromine; andA is a divalent radical of the formula: ##STR2## wherein R.sub.2 is hydrogen, methyl, or ethyl, and m and n, independently, are an integer from 0 to 4, provided that m+n cannot be greater than 4; --(CH.sub.2).sub.p --D--(CH.sub.2).sub.Type: GrantFiled: June 1, 1981Date of Patent: June 12, 1984Assignee: Merrell Toraude et CompagnieInventor: Philippe Bey