Amidine, Azomethine, Ketimine Or Oxime In Acid Moiety Patents (Class 560/35)
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Patent number: 4604128Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: m is an integer selected from 1 to 4;n is zero or an integer selected from 1 to 4;X are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, alkylthio, sulfamoyl, substituted sulfamoyl, amino, substituted amino, the group --(CH.sub.2).sub.p C(.dbd.A)Z in which p is zero or one A is oxygen or sulfur, and Z is hydrogen, hydroxy, alkoxy, alkylthio, alkyl, substituted alkyl, amino or substituted amino, the group --NHC(.dbd.B)NR.sup.7 R.sup.8 in which B is oxygen or sulfur and R.sup.7 and R.sup.8 are hydrogen or alkyl;R.sup.1 is selected from hydrogen, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl; andR.sup.4 is selected from hydrogen, halogen, alkyl, cyano and alkoxycarbonyl.Type: GrantFiled: September 10, 1985Date of Patent: August 5, 1986Assignee: ICI Australia LimitedInventors: Keith G. Watson, John D. Wishart, Graeme J. Farquharson, Graham J. Bird, Lindsay E. Cross
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Patent number: 4598077Abstract: Amidine derivatives of the formula ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, represent each a hydrogen atom or a lower alkyl group, or R.sub.1 and R.sub.2 together with an intermediary carbon atom and/or hetero atom may form a ring; X represents ##STR2## (wherein R.sub.8 represents a hydrogen atom, a lower alkyl group, or --CH.sub.2 COOR.sub.9, where R.sub.9 represents a hydrogen atom or a lower alkyl group; Z represents a single bond, --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, or --CH.dbd.CH--); R.sub.3 represents a hydrogen or chlorine atom, methoxy group, nitro group, or amino group; Y represents --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 O--, or --OCH.sub.2 --; R.sub.4 represents a hydrogen atom, methoxy group, benzoyl group, nitro group, or amino group; and R.sub.5, R.sub.6 and R.sub.Type: GrantFiled: December 14, 1984Date of Patent: July 1, 1986Assignee: Torii & Co. Ltd.Inventors: Setsuro Fujii, Takuo Sato, Hiroyuki Kawamura, Takashi Yaegashi, Masateru Kurumi, Takuo Aoyama
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Patent number: 4596823Abstract: Novel compounds have a formula (I) ##STR1## wherein ##STR2## represents a bicyclo[2,2,1]hept-2Z-ene, bicyclo[2,2,1]heptane, 7-oxabicyclo[2,2,1]hept-2Z-ene, 7-oxabicyclo[2,2,1]heptane, bicyclo[2,2,2]oct-2Z-ene or bicyclo[2,2,2]octane substituted at the 5-position by the group R.sup.1 and at the 6-position by the group C(R.sup.2).dbd.NR, a 6,6-dimethyl-bicyclo[3,1,1]heptane substituted at the 5-position by the group R.sup.1 and at the 6-position by the group C(R.sup.2).dbd.NR or at the 5-position by the group C(R.sup.2).dbd.NR and at the 6-position by the group R.sup.1, a cyclohex-1-ene or cyclohexane substituted at the 4-position by the group R.sup.1 and at the 5-position by the group C(R.sup.2).dbd.NR, or a 1-hydroxycyclopentane substituted at the 2-position by the group R.sup.1 and at the 2-position by the group C(R.sup.2).dbd.NR, R.sup.1 is a 6-caboxyhex-2-enyl group or a modification thereof as defined herein, R.sup.Type: GrantFiled: February 12, 1982Date of Patent: June 24, 1986Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 4593118Abstract: 2,3-Diaminocarboxylic acid compounds are prepared by (A) nitrosating a .beta.-keto ester to form a 3-keto-2-oximino ester, (B) converting the resultant oxime to a protected 2-amine, (C) reductively aminating the 3-position of the protected 2-amine to form a 2,3-diaminocarboxylic acid ester wherein the 2-amino group is protected, and (D) when desired, treating the 2,3-diaminocarboxylic acid ester to deprotect one or more of the amino and carboxyl groups.Type: GrantFiled: March 6, 1985Date of Patent: June 3, 1986Assignee: Ethyl CorporationInventor: Beverly A. Bauer
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Patent number: 4585887Abstract: Process for the production of an optically active 3-aminocarboxylic acid ester from a .beta.-keto acid ester. The .beta.-keto acid ester is converted with a chiral amine into the corresponding enamine. The enamine is converted by hydrogenation in the presence of a platinum catalyst into the corresponding N-substituted amino acid esters. Such ester mix is converted by means of HCl gas into the hydrochlorides. The latter are neutralized. Then by liberation and isolation from the neutralized products by hydrogenolysis in the presence of a palladium catalyst, the desired optically-active 3-aminocarboxylic acid ester is obtained.Type: GrantFiled: December 4, 1984Date of Patent: April 29, 1986Assignee: Lonza Ltd.Inventors: Synese Jolidon, Thomas Meul
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Patent number: 4584014Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is hydrogen, alkyl, cycloalkyl, phenylalkyl, alkoxyalkyl, alkoxyaryl, aryl or an agronomically acceptable cation; R.sup.2 and R.sup.3 are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted phenylalkyl, carboxy, alkoxycarbonyl or phenyl group; X is hydrogen, fluoro, bromo, chloro or iodo atom; Y is a hydrogen, fluoro, bromo, chloro, iodo, alkyl, cycloalkyl, carboxy, alkoxycarbonyl, phenylalkyl, alkenyl and alkynyl group, wherein the alkyl, cycloalkyl, phenylalkyl and phenyl group may have up to three optional substituents; and B is hydrogen, carboxy, alkoxycarbonyl, methylene (--CH.sub.2 R.sup.4) or CZZ.sup.1 Z.sup.2 group wherein R.sup.4 is an alkyl or alkenyl group and Z, Z.sup.1 and Z.sup.2 are each independently a hydrogen, fluoro, bromo, chloro or iodo atom, provided that Z, Z.sup.1, Z.sup.2, X and Y are not all hydrogens.Type: GrantFiled: July 2, 1984Date of Patent: April 22, 1986Assignee: Rohm and Haas CompanyInventor: Dennis R. Patterson
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Patent number: 4576732Abstract: The present invention is characterized by a smectic liquid crystal compound represented by the following formula: ##STR1## wherein R is selected from alkyl and alkoxy groups; X from ##STR2## m and n are natural numbers; and R* is an optically active group containing an asymmetric carbon atom, and a liquid crystal composition containing said compound as a component. This compound is excellent in optical stability and high-speed response.Type: GrantFiled: November 28, 1983Date of Patent: March 18, 1986Assignee: Hitachi, Ltd.Inventors: Masato Isogai, Shintaroo Hattori, Kishiroo Iwasaki, Teruo Kitamura, Akio Mukoh, Takashi Inukai, Kenji Furukawa, Kanetsugu Terashima, Shinichi Saitoh
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Patent number: 4565818Abstract: A 6- and/or 7-oxy-trans-1,2,3,4,4a,5,10,10a-octahydro-benzo[g]quinoline in which the 3-position is substituted by an optionally amidated carboxy group, an optionally etherified hydroxymethyl group, a cyanomethyl group, an alkyl- or aryl-thiomethyl group or a sulfamoylamino or carbamoylamino group, or a physiologically-hydrolysable and -acceptable ester thereof. The subject compounds are useful as pharmaceuticals, in particular as prolactin secretion inhibitors, dopaminergic agents ad dopamine receptor stimulating agents.Type: GrantFiled: October 14, 1982Date of Patent: January 21, 1986Assignee: Sandoz Ltd.Inventors: Rene Nordmann, Trevor J. Petcher
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Patent number: 4564385Abstract: This invention relates to certain herbicidally active substituted diphenyl ether oxime derivatives, herbicidal compositions of the same and the use thereof for preemergence and postemergence control of noxious plants, i.e., weeds.Type: GrantFiled: January 28, 1985Date of Patent: January 14, 1986Assignee: PPG Industries, Inc.Inventor: Dennis K. Krass
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Patent number: 4552898Abstract: Compounds useful in treating cardiovascular disorders are the carboxylic acids depicted in formulas (1) and (2) ##STR1## as well as their pharmaceutically acceptable, non-toxic salts and esters, wherein:n is an integer from one to four;R.sub.1 is hydroxy;R.sub.2 is hydrogen; orR.sub.1 and R.sub.2 together are an oxo group;R.sub.3 is ##STR2## wherein A is --CH.sub.2 --CH.sub.2 --; trans--CH.dbd.CH--; --C.tbd.C--; andR.sub.4 is linear or branched alkyl of one to twelve carbons, preferably 1-10 carbons, most preferably 3-8 carbons, cycloalkyl of three to eight carbons; phenyl optionally substituted with one or two identical substituents selected from the group consisting of lower alkyl, lower alkoxy, hydroxy, trifluoromethyl, and halo; or phenylloweralkyl optionally substituted with one or two identical substituents selected from the group consisting of lower alkyl, lower alkoxy, hydroxy, trifluoromethyl, and halo.Type: GrantFiled: August 19, 1983Date of Patent: November 12, 1985Assignee: Syntex (U.S.A.) Inc.Inventors: Tsung-Tee Li, Michael Marx
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Patent number: 4548756Abstract: Novel oxime ethers and oxime esters of the formula I given herein have various advantageous effects with regard to stimulation of plant growth, particularly in the early stage of development of the plant. Furthermore, such compounds have the property of rendering, in the sense of an antidote action, agricultural chemicals which would otherwise damage the plants (phytotoxic chemicals) more compatible with the cultivated plants. Herbicides that are insufficiently selective can be used for example in the presence of such oxime derivatives in specific cultivated crops for combating weeds, without disadvantageous consequences for the cultivated plants.Type: GrantFiled: December 7, 1984Date of Patent: October 22, 1985Assignee: Ciba Geigy CorporationInventor: Henry Martin
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Patent number: 4537989Abstract: A compound of the formula ##STR1## wherein X.sup.1 is a free or an esterified carboxyl group, or a group of the formula: ##STR2## (R.sup.a and R.sup.b are each independently a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, a benzyl group, a phenyl group, a phenyl group substituted with a halogen atom or a C.sub.1 -C.sub.4 alkyl group, or, when taken together with the adjacent nitrogen atom to which they are attached, they represent a 5 to 7 membered saturated heterocyclic group), Y is a group of the formula: ##STR3## (R.sup.6 is a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group) or ##STR4## (R.sup.6 is as defined above), R.sup.1 is a hydrogen atom, a hydroxyl group or a protected hydroxyl group, R.sup.2 is a hydrogen atom or R.sup.1 and R.sup.2, when taken together, mean a single linkage to form a double bond between the carbon atoms which they are linked, R.sup.3 is a hydroxyl group or a protected hydroxyl group, R.sup.4 is a hydrogen atom or a C.sub.1 -C.sub.Type: GrantFiled: April 15, 1983Date of Patent: August 27, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Keiichi Ono, Akihiko Sugie, Masami Muraoka, Michihiro Yamamoto
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Patent number: 4530798Abstract: Novel oxime ethers and oxime esters of the formula I given herein have various advantageous effects with regard to stimulation of plant growth, particularly in the early stage of development of the plant. Furthermore, such compounds have the property of rendering, in the sense of an antidote action, agricultural chemicals which would otherwise damage the plants (phytotoxic chemicals) more compatible with the cultivated plants. Herbicides that are insufficiently selective can be used for example in the presence of such oxime derivatives in specific cultivated crops for combating weeds, without disadvantageous consequences for the cultivated plants.Type: GrantFiled: September 30, 1982Date of Patent: July 23, 1985Assignee: Ciba-Geigy CorporationInventor: Henry Martin
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Patent number: 4514416Abstract: Amidino compounds represented by the formula (I) ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful antitrypsine, antiplasmin, antikallikrein and anti-thrombin agents. Having strong anti-Cl (Clr, Cls) activities and an anticomplement activity, they are also useful as anticomplement agents. These amidino compounds are prepared by usual esterification of carboxylic acid compounds represented by the formula (II)R.sub.1 --COOH (II)with amidinophenol compound (III) and, if necessary, can be transformed into pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: May 21, 1984Date of Patent: April 30, 1985Assignee: Torii & Co. Ltd.Inventors: Setsuro Fujii, Takashi Yaegashi, Toyoo Nakayama, Yojiro Sakurai, Shigeki Nunomura, Toshiyuki Okutome
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Patent number: 4509970Abstract: Novel substituted phenylphosphinyloxy- and phenylphosphinylthio-iminocarboxylates, synthesis thereof, intermediates therefor, and the use of said novel compounds for the control of weeds.Type: GrantFiled: December 17, 1981Date of Patent: April 9, 1985Assignee: Zoecon CorporationInventor: Shy-Fuh Lee
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Patent number: 4504305Abstract: A compound having the general formula ##STR1## wherein R.sub.1 is alkyl having 1-3 carbon atoms;R.sub.2 is alkyl having 1-3 carbon atoms, allyl, propargyl or haloalkenyl; andA is selected from the group consisting of ##STR2## wherein R.sub.3 is --SO.sub.2 R.sub.6 group, ##STR3## R.sub.4 is hydrogen, alkyl having 1-6 carbon atoms; phenyl or halophenyl; R.sub.5 is alkyl having 1-3 carbon atoms; X is oxygen or sulfur; and n is 0 or 1; wherein R.sub.6 is alkyl having 1-6 carbon atoms, haloalkyl having 1-6 carbon atoms or propenyl; R.sub.7 is hydrogen or alkyl having 1-4 carbon atoms; R.sub.8 is hydrogen, alkyl having 1-6 carbon atoms; propenyl or methoxy; R.sub.9 is hydrogen, alkyl having 1-8 carbon atoms, haloalkyl having 1-3 carbon atoms, alkoxy having 1-6 carbon atoms, propenyl or phenyl substituted with methyl; and Y and Z are oxygen or sulfur; and a metal salt or a quaternary ammonium salt of a compound defined herein above.The compound is useful as a herbicide.Type: GrantFiled: December 27, 1982Date of Patent: March 12, 1985Assignee: Nippon Soda Co., Ltd.Inventors: Isao Iwataki, Akira Nakayama, Minoru Kaeriyama, Hisao Ishikawa, Hideo Hosaka, Kenichi Kohara
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Patent number: 4504671Abstract: Aldoxime or ketoxime-O-alkanoic acid is prepared by transoximation of an aldehyde or ketone, the reaction being conducted in a liquid phase at a pressure below one atmosphere. Conversion of the aldoxime or ketoxime-O-alkanoic acid to the ester or salt form is also described.Type: GrantFiled: October 15, 1982Date of Patent: March 12, 1985Assignee: PPG Industries, Inc.Inventors: Dennis K. Krass, John C. Crano, Melvin S. Newman
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Patent number: 4503232Abstract: The invention provides a novel method for the preparation of an .alpha.-ketoamide imine having a characteristic structure expressed by the formula ##STR1## in which R is a group such as an alkyl, aryl or the like group, in a one-step reaction in which a halogen-containing organic compound reacts with a primary amine and carbon monoxide in the presence of a carbonylation catalyst. The product compound is useful as an intermediate for the synthesis of various kinds of organic compounds including medicines and agricultural chemicals.Type: GrantFiled: September 24, 1982Date of Patent: March 5, 1985Assignee: Agency of Industrial Science & TechnologyInventors: Toshiaki Kobayashi, Masato Tanaka
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Patent number: 4497745Abstract: Novel oxime ethers and oxime esters of the formula I given herein have various advantageous effects with regard to stimulation of plant growth, particularly in the early stage of development of the plant. Furthermore, such compounds have the property of rendering, in the sense of an antidote action, agricultural chemicals which would otherwise damage the plants (phytotoxic chemicals) more compatible with the cultivated plants. Herbicides that are insufficiently selective can be used for example in the presence of such oxime derivatives in specific cultivated crops for combating weeds, without disadvantageous consequences for the cultivated plants.Type: GrantFiled: September 30, 1982Date of Patent: February 5, 1985Assignee: Ciba-Geigy CorporationInventor: Henry Martin
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Patent number: 4484008Abstract: This invention relates to an improvement in the process of isolating certain diphenyl ethers from an aprotic organic solvent by the addition of a diphenyl ether phase forming amount of water to a reaction mixture comprising a liquid phase of the diphenyl ether dissolved in the solvent.Type: GrantFiled: September 30, 1982Date of Patent: November 20, 1984Assignee: PPG Industries, Inc.Inventors: James A. Cook, Jr., James A. Manner
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Patent number: 4482496Abstract: 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: GrantFiled: June 1, 1982Date of Patent: November 13, 1984Assignee: Ciba-Geigy CorporationInventor: Kurt Weber
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Patent number: 4479900Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is lower alkyl or benzyl. R.sup.2 is lower alkoxy, benzyloxy, or the group ##STR2## where R.sup.3 is lower alkoxy; and Ar is phenyl optionally substituted with 1 to 3 substituents independently selected from halogen, trihalomethyl, nitro or lower alkyl, show plant growth regulating activity.Type: GrantFiled: April 29, 1983Date of Patent: October 30, 1984Assignee: Chevron Research CompanyInventor: Tatao Luo
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Patent number: 4478758Abstract: Schiff bases of aminocycloalkanecarboxylic acid esters of the formula ##STR1## where R, R.sup.1, R.sup.2, m and n have the meanings given in the description, are prepared by a novel process. The compounds are intermediates for the preparation of the corresponding aminocycloalkanecarboxylic acids and of esters thereof.Type: GrantFiled: June 29, 1982Date of Patent: October 23, 1984Assignee: BASF AktiengesellschaftInventors: Gunter Schulz, Ernst Buschmann, Bernd Zeeh
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Patent number: 4474764Abstract: New 3-N-acyl derivatives of 3-amino-2-hydroxy-4-phenylbutanoic acid are provided, which exhibit analgesic activity and are affective to enhance the morphine analgesia.Type: GrantFiled: September 28, 1982Date of Patent: October 2, 1984Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Hamao Umezawa, Tomio Takeuchi, Takaaki Aoyagi, Mitsugu Hachisu, Kenji Kawamura, Shunzo Fukatsu, Yasuharu Sekizawa
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Patent number: 4466822Abstract: Novel oxime ethers and oxime esters of the formula I given herein have various advantageous effects with regard to stimulation of plant growth, particularly in the early stage of development of the plant. Furthermore, such compounds have the property of rendering, in the sense of an antidote action, agricultural chemicals which would otherwise damage the plants (phytotoxic chemicals) more compatible with the cultivated plants. Herbicides that are insufficiently selective can be used for example in the presence of such oxime derivatives in specific cultivated crops for combating weeds, without disadvantageous consequences for the cultivated plants.Type: GrantFiled: March 11, 1980Date of Patent: August 21, 1984Assignee: Ciba-Geigy CorporationInventor: Henry Martin
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Patent number: 4443372Abstract: 1-Alkyl derivatives of 3-aryloxy-4-(2-carbalkoxy)-phenyl-azet-2-ones of the formula: ##STR1## wherein R.sub.1 is methyl or ethyl; R.sub.2 is lower alkyl; and X.sub.1 and X.sub.2 are independently hydrogen or halogen, are effective as plant growth regulators.Type: GrantFiled: June 23, 1982Date of Patent: April 17, 1984Assignee: Chevron Research CompanyInventors: Tatao Luo, Louis Russo, Francis J. Freenor, III
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Patent number: 4440566Abstract: Substituted 2-[1-(oxyamino)alkylidene]-cyclohexane-1,3-diones have herbicidal activity against grassy weeds.Type: GrantFiled: August 9, 1982Date of Patent: April 3, 1984Assignee: Chevron Research CompanyInventor: Tatao Luo
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Patent number: 4439446Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is a hydrogen atom; or a hydrocarbyl group; m and n each is 0 or 1 and m+n is 1 or 2; and D is a hydrogen atom; a cyano group; or an ethynyl group, are useful as pesticides.Type: GrantFiled: September 13, 1982Date of Patent: March 27, 1984Assignee: Shell Oil CompanyInventor: Samuel B. Soloway
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Patent number: 4438136Abstract: Novel bicyclo [2,2,1] heptanes and hept-2-enes are substituted at the 5-position by a 6-carboxyhex-2-enyl group or a modification thereof, and at the 6-position by a grouping --C(R).dbd.N--NHCO--(NH).sub.a --R' in which R is hydrogen, an aliphatic hydrocarbon residue, an aromatic residue or an aliphatic hydrocarbon residue substituted by an aromatic residue, a is 0 or 1 and R' is an aliphatic hydrocarbon residue, an aromatic residue, or an aliphatic hydrocarbon residue substituted directly or through an oxygen or sulphur atom by an aromatic residue. The compounds are of value for use in pharmaceutical compositions particularly in the context of the inhibition of thromboxane activity.Type: GrantFiled: September 17, 1982Date of Patent: March 20, 1984Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 4430345Abstract: Novel bicyclo [2,2,1] heptanes and hept-2Z-enes are substituted at the 5-position by a 6-carboxyhex-2-enyl group or a modification thereof, and at the 6-position by an aldoxime or ketoxime group which is O-substituted by an aliphatic hydrocarbon residue, an aromatic residue, or an aliphatic hydrocarbon residue substituted directly or through an oxygen or sulphur atom by an aromatic residue. Such compounds may be prepared by the action of an oximating agent on an intermediate which is substituted at the 6-position by an aldehydic or ketonic carbonyl group. The compounds are of value for use in pharmaceutical compositions particularly in the context of the inhibition of thromboxane activity.Type: GrantFiled: September 30, 1982Date of Patent: February 7, 1984Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 4425360Abstract: The present invention provides pyruvic acid oximes of the general formula: ##STR1## wherein R is a hydrogen atom, a C.sub.3 -C.sub.8 cycloalkyl, C.sub.1 -C.sub.6 alkoxy, cinnamyloxy, phenylamino, phenyl-N-alkylamino or phenylthio radical or an aryl or aryloxy radical, the aryl moiety of which can be substituted one or more times by C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halogen, hydroxyl, trifluoromethyl, amino, acetylamino, nitrile, nitro or methylenedioxy, A is a straight-chained or branched, saturated or unsaturated aliphatic hydrocarbon chain containing up to 10 carbon atoms, which can be substituted one or more times by halogen or hydroxyl, and R.sub.1 is a C.sub.1 -C.sub.8 alkyl radical, which can be substituted one or more times by halogen, hydroxyl, nitrile, phenyl or carboxyl, or is a nitrile or formyl group, with the proviso that when R--A-- is a methyl or ethyl radical, R.sub.1 is not a methyl radical or a nitrile group and when R--A-- is a benzyl radical, R.sub.Type: GrantFiled: September 8, 1981Date of Patent: January 10, 1984Assignee: Boehringer Mannheim GmbHInventors: Hans P. Wolff, Ruth Heerdt, Manfred Hubner, deceased, Hans Kuhnle, Felix H. Schmidt
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Patent number: 4423241Abstract: Novel 2,6-dihalogenated benzylidene aminooxyacetic acid compounds and derivatives thereof, have been found to have exceptional herbicidal activity, particularly in regard to nutsedge control.Type: GrantFiled: April 9, 1982Date of Patent: December 27, 1983Assignee: Union Carbide CorporationInventor: Paul J. Caruso
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Patent number: 4423068Abstract: Compounds useful in treating cardiovascular disorders are the carboxylic acids depicted in formulas (1) and (2) ##STR1## as well as their pharmaceutically acceptable, non-toxic salts and esters, wherein:n is an integer from one to four;R.sub.1 is hydroxy;R.sub.2 is hydrogen; orR.sub.1 and R.sub.2 together are an oxo group;R.sub.3 is ##STR2## wherein A is --CH.sub.2 --CH.sub.2 --; trans-CH.dbd.CH--; --C.tbd.C--; andR.sub.4 is linear or branched alkyl of one to twelve carbons, cycloalkyl of three to eight carbons; phenyl optionally substituted with one or two identical substituents selected from the group consisting of lower alkyl, lower alkoxy, hydroxy, trifluoromethyl, and halo; or optionally substituted phenylalkyl.Type: GrantFiled: July 14, 1982Date of Patent: December 27, 1983Assignee: Syntex (U.S.A.) Inc.Inventors: Tsung-tee Li, Michael Marx
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Patent number: 4415743Abstract: Novel oxime ethers and oxime esters of the formula I given herein have various advantageous effects with regard to stimulation of plant growth, particularly in the early stage of development of the plant. Furthermore, such compounds have the property of rendering, in the sense of an antidote action, agricultural chemicals which would otherwise damage the plants (phytotoxic chemicals) more compatible with the cultivated plants. Herbicides that are insufficiently selective can be used for example in the presence of such oxime derivatives in specific cultivated crops for combating weeds, without disadvantageous consequences for the cultivated plants.Type: GrantFiled: September 30, 1982Date of Patent: November 15, 1983Assignee: Ciba-Geigy CorporationInventor: Henry Martin
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Patent number: 4400520Abstract: A process for the preparation of an isoindoline derivative of the following general formula (II): ##STR1## wherein R.sup.2 is a hydrogen atom or lower alkyl group and X is a carboxyl group, carboalkoxy group, amide group or cyano group, which comprisescycling a benzylidene derivative of the following general formula (I) ##STR2## wherein R.sup.1 is a hydrogen atom or lower alkyl group, and R.sup.2 and X are as defined above, in the presence of a reducing agent such as sodium boron hydride. In one embodiment, the benzylidene derivative may be substituted by a reaction mixture containing the same, the reaction mixture being prepared by reacting o-phthalaldehydic acid or its ester with an aniline derivative.Type: GrantFiled: September 4, 1981Date of Patent: August 23, 1983Assignee: Hisamitsu Pharmaceutical Co., Inc.Inventors: Kanji Noda, Akira Nakagawa, Toshiharu Motomura, Hiroyuki Ide
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Patent number: 4400394Abstract: Compounds of the formula: ##STR1## in which X.sub.1, X.sub.2 and X.sub.3, which are identical or different, each represent hydrogen, halogen, methyl, or methoxy, n represents an integer from 1 to 10, and R represents hydroxyl, OM, NH.sub.2, NH(CH.sub.2).sub.3 --COOH, --NH(CH.sub.2).sub.3 --COOM, (where M represents an alkali metal atom), NH(CH.sub.2).sub.3 --COOC.sub.2 H.sub.5, NH-cycloalkyl, NH-phenyl, NH-benzyl (where the benzyl radical is unsubstituted or substituted by halogen or trifluoromethyl), NH-alkyl, N(alkyl).sub.2 and N-(alkyl)-(benzyl), the aforesaid alkyls being straight or branched and having from 1 to 4 carbon atoms and the aforesaid cycloalkyls having from 3 to 6 carbon atoms, except that when X.sub.1 and X.sub.3 are both hydrogen, n is 1 and R is OH, X.sub.2 is not chlorine in the 5-position are useful in the treatment of epilepsy by oral or parenteral administration.Type: GrantFiled: August 3, 1981Date of Patent: August 23, 1983Assignee: SynthelaboInventors: Jean-Pierre Kaplan, Naurice Jalfre, Don P. Giudicelli
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Patent number: 4386954Abstract: This invention is directed to diphenyl ethers having in the 3' position a radical of the formula: ##STR1## The products are prepared by reacting a 3'-halocarbonyl compound with an appropriately substituted oxime. These compounds and their agronomically acceptable salts and compositions containing these compounds as active ingredients are selective herbicides.Type: GrantFiled: August 17, 1981Date of Patent: June 7, 1983Assignee: Rohm and Haas CompanyInventors: John W. Ashmore, Ted T. Fujimoto
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Patent number: 4382955Abstract: A novel compound of 4-[N-(3',4'-dihydroxybenzylidene) aminomethyl]cyclohexane-1-carboxylic acid or a salt or an ester thereof which has specific pharmacologic activities, a method for preparing thereof and a pharmaceutical composition comprising thereof as an active ingredient are provided.Type: GrantFiled: May 26, 1981Date of Patent: May 10, 1983Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Hitoshi Takita, Yutaka Mukaida, Sakuo Noda, Hidetoshi Kobayashi
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Patent number: 4377594Abstract: A novel compound of 4-[N-(substituted-benzylidene)aminomethyl]cyclohexane-1-carboxylic acid or a salt or an ester thereof which has specific pharmacologic activities, a method for preparing thereof and a pharmaceutical composition comprising thereof as an active ingredient are provided.Type: GrantFiled: May 26, 1981Date of Patent: March 22, 1983Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Hitoshi Takita, Yutaka Mukaida, Sakuo Noda, Hidetoshi Kobayashi
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Patent number: 4372776Abstract: Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.3 each is hydrogen or R.sup.1 and R.sup.3 together form a second carbon-to-nitrogen bond, R.sup.2 is hydrogen or cyano, R.sup.4 is alkyl and Ar is one of certain aromatic moieties.The compounds can be used as abscission agents for the loosening of fruit and/or leaves on plants.Type: GrantFiled: October 16, 1981Date of Patent: February 8, 1983Assignee: Shell Oil CompanyInventors: Janet A. Day, Robert J. G. Searle
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Patent number: 4368332Abstract: Novel bicyclo [2,2,1] heptanes and hept-2Z-enes are substituted at the 5-position by a 6-carboxyhex-2-enyl group or a modification thereof, and at the 6-position by an aldoxime or ketoxime group which is O-substituted by an aliphatic hydrocarbon residue, an aromatic residue, or an aliphatic hydrocarbon residue substituted directly or through an oxygen or sulphur atom by an aromatic residue. Such compounds may be prepared by the action of an oximating agent on an intermediate which is substituted at the 6-position by an aldehydic or ketonic carbonyl group. The compounds are of value for use in pharmaceutical compositions particularly in the context of the inhibition of thromboxane activity.Type: GrantFiled: September 3, 1980Date of Patent: January 11, 1983Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 4344789Abstract: Compounds, such as 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitroacetophenone oxime-O-(acetic acid, methyl ester) and 5-(2-chloro-4-trifluoromethylphenoxy)-2-chloroacetophenone oxime-O-(acetic acid, methyl ester), are useful for postemergence and preemergence control of weeds, and are represented by Formula I of the application.Type: GrantFiled: April 15, 1980Date of Patent: August 17, 1982Assignee: PPG Industries, Inc.Inventor: Dennis K. Krass
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Patent number: 4332958Abstract: An improved process for preparing 1-aminocyclopropane-1-carboxylic acid, which acid is a plant growth regulator.Type: GrantFiled: June 19, 1981Date of Patent: June 1, 1982Assignee: Zoecon CorporationInventor: Shy-fuh Lee
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Patent number: 4324579Abstract: Amidoximes of the formula ##STR1## are disclosed. R represents a hydrogen atom on a lower alkyl (C.sub.1 -C.sub.4) or phenyl; R.sub.1 represents lower alkyl or a metal atom and Ar represents substituted or unsubstituted phenyl or a five-membered substituted or unsubstituted aromatic heterocyclic group where the hetero atom is selected from the group O, S and N. The compounds have phytohormonal activity at low dosages in plants and herbicidal activity at higher levels.Type: GrantFiled: January 29, 1980Date of Patent: April 13, 1982Assignee: PhilargoInventors: Daniel Farge, Jean Leboul, Yves Le Goff, Gilbert Poiget
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Patent number: 4322364Abstract: A process for the production of a modified isocyanate by reacting a composition containing carbodiimide groups and free isocyanate groups with a diester of an aliphatic dicarboxylic acid in the presence of oxalic or formic acid.The process permits the production of liquid forms of diphenylmethane diisocyanate useful in the manufacture of polyurethanes.Type: GrantFiled: January 2, 1981Date of Patent: March 30, 1982Assignee: Imperial Chemical Industries LimitedInventors: Jeffrey Hughes, Gerard J. Murray
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Patent number: 4317835Abstract: There is disclosed pharmaceutical preparations and a method of using same in the treatment of inflammation and/or pain, e.g., treating rheumatic affections, with novel substituted alkylidene-aminooxyalkyl carboxylic acid esters.Type: GrantFiled: September 26, 1980Date of Patent: March 2, 1982Assignee: Duphar International Research B.V.Inventors: Jan van Dijk, Johannes M. A. Zwagemakers
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Patent number: 4312862Abstract: Novel therapeutically active derivatives of benzamide, having the general formula ##STR1## in which R.sub.1 and R.sub.2, independently of each other, are hydrogen or a lower alkyl group, R.sub.3 is a phenyl or lower alkyl or lower alkenyl group, R.sub.4 is a halogen or a trifluoromethyl or nitro-group, R.sub.5 is a sulphamoyl or carboxyl or carboxy-alkyl group, and the potassium salts of these derivatives.These compounds are diuretics and hypotensors (blood pressure depressants) and they lower the angiotensin and renin functions, with prolonged action.Type: GrantFiled: July 19, 1979Date of Patent: January 26, 1982Assignee: Debiopharm SAInventors: William P. Purcell, Harlie A. Parish, Jr.
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Patent number: 4304936Abstract: 3-Phenoxy-.alpha.-phenoxy-alkancarboxylic acid derivatives of the formula ##STR1## are disclosed as possessing a surprising selective herbicidal activity. In the formula, Hal is a halogen atom, m is an integer 1, 2 or 3, Y is a hydrogen or halogen atom or the cyano group, Z is a halogen atom or the cyano group, R.sub.1 is hydrogen or C.sub.1 -C.sub.8 alkyl, and R is an acid function. Methods are disclosed for combatting weeds in mono- and dicotyledonous cultures such as cereals, corn, rice, soya and cotton, which comprise applying to the locus to be protected from weeds a dosage of from 0.1 to 10.0 kilograms per hectare of the above compounds.Type: GrantFiled: October 11, 1979Date of Patent: December 8, 1981Assignee: Ciba-Geigy CorporationInventors: Otto Rohr, Georg Pissiotas, Beat Bohner, Kurt Burdeska
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Patent number: 4298760Abstract: An improved process for preparing 1-aminocyclopropane-1-carboxylic acid, which acid is a plant growth regulator.Type: GrantFiled: August 14, 1980Date of Patent: November 3, 1981Assignee: Zoecon CorporationInventor: Shy-Fuh Lee
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Patent number: 4297502Abstract: An aromatic bisazomethine prepared from the disubstituted benzidines and aromatic aldehydes, characterized by the general formula ##STR1## wherein each R=COOCH.sub.3, COOC.sub.2 H.sub.5, COOH, CH.sub.2 Cl, CHCl.sub.2, CH.sub.2 Br, CCl.sub.3, Cl or Br andeach R'=Cl, OCH.sub.3 or CH.sub.3.Type: GrantFiled: June 19, 1980Date of Patent: October 27, 1981Assignee: Dynamit Nobel AktiengesellschaftInventors: Hans-Joachim Herrmann, Gunther Meyer, Klaus-Dieter Steffen