Halogen Attached Directly To The Diazine Ring By Nonionic Bonding Patents (Class 544/313)
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Patent number: 5047407Abstract: Methods and compositions for preventing or treating human immunodeficiency virus (HIV) infections characterized by 2-substituted-5-substituted-1,3-oxathiolanes.Type: GrantFiled: February 8, 1989Date of Patent: September 10, 1991Assignee: IAF BioChem International, Inc.Inventors: Bernard Belleau, Nghe Nguyen-Ba
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Patent number: 5041449Abstract: There are provided novel 2-substituted-4-substituted-1,3-dioxolanes which are particularly useful as antiviral agents.Type: GrantFiled: June 29, 1990Date of Patent: August 20, 1991Assignee: IAF BioChem International, Inc.Inventors: Bernard Belleau, Dilip Dixit, Nghe Nguyen-Ba
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Patent number: 5041156Abstract: The present invention is concerned with heterocyclic compounds, namely 3-aryluracils of the general formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and Q are as described herein, as well as salts thereof and their manufacture, weed control compositions.Type: GrantFiled: June 16, 1989Date of Patent: August 20, 1991Assignee: Ciba-Geigy CorporationInventors: Milos Suchy, Jean Wenger, Paul Winternitz, Martin Zeller
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Patent number: 5032680Abstract: 2'-Deoxy-5-fluorouridine derivatives of the formula ##STR1## wherein, R.sup.1 is hydrogen atom or an acyl group and R.sup.2 and R.sup.3 are respectively hydrogen atom, an acyl group or a group of the formula ##STR2## wherein X.sup.1 and X.sup.2 are respectively oxygen atom or sulfur atom; R.sup.4 is a phenyl group, a benzyl group or a naphthyl group each of which may be substituted by an alkyl group, an alkoxyl group, an alkoxycarbonyl group, an alkylthio group, and acyl group, a halogen atom, trifluoromethyl group, nitro group, cyano group, carboxyl group and/or methylenedioxy group and R.sup.5 is an alkyl group, an alkenyl group or one of the groups represented by R.sup.4 which is the same as or different from R.sup.4, at least one of R.sup.2 and R.sup.3 being a group of the formula ##STR3## which exhibit excellent antitumour activities and have lower toxicity, methods of the production thereof and antitumour compositions containing said 2'-deoxy-5-fluorouridine derivatives.Type: GrantFiled: February 24, 1989Date of Patent: July 16, 1991Assignees: Kuraray Co., Ltd., Taiho Pharmaceutical Co., Ltd.Inventors: Tsutomu Kawai, Fumio Mori, Setsuo Takeda, Hitoshi Saito, Norio Unemi
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Patent number: 5019151Abstract: A 2-phenoxypridimine derivative having the formula: ##STR1## wherein X is a halogen atom or ##STR2## wherein X.sup.1 is a halogen atom, a lower alkyl group or a lower alkoxy group and k is 0, 1, or 2; R.sup.1 is a hydrogen atom, a benzyl group, --(CH.sub.2).sub.m R.sup.3 is a cyano group, a formyl group, a dialkylamino group, a phenyl group, a pyridyl group, a trimethylsilyl group, a naphthyl group, an alkoxycarbonyl group, a benzoyl group, an alkylthio group, a phenylthio group, an alkylsulfonyl group or a benzyloxy group and m is 1, 2, or ##STR3## wherein R.sup.4 is a hydrogen atom or a lower alkyl group, R.sup.5 is a lower alkyl group or ##STR4## wherein X.sup.2 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or a nitro group, n is 0 or 1, provided that when R.sup.5 is an alkyl group, n is 1; and R.sup.2 is a chlorine atom or a methoxy group, provided that when R.sup.1 is a hydrogen atom or a benzyl group, X is ##STR5## and R.sup.2 is a methoxy group, when R.sup.Type: GrantFiled: April 19, 1990Date of Patent: May 28, 1991Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Nobuhide Wada, Yoshihiro Saito, Shoji Kusano, Yasufumi Toyokawa, Takeshige Miyazawa, Satoru Takahashi, Takayoshi Takehi
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Patent number: 5017211Abstract: The invention is concerned with novel compounds of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 have the significances given in the description, as well as enol ethers and salts thereof and their manufacture, weed control compositions which contain such compounds as the active substance and the use of the active substances or compositions for the control of weeds. The invention is also concerned with certain novel starting materials and their production.Type: GrantFiled: May 19, 1989Date of Patent: May 21, 1991Assignee: Ciba-Geigy CorporationInventors: Jean Wenger, Paul Winternitz, Martin Zeller
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Patent number: 5013828Abstract: 2'-Deoxy-3',5'-diacyl-5-fluorouridines useful as antitumor medicines or intermediates thereof are easily and efficiently obtained by first fluorinating 2'-deoxyuridine in aqueous solution with fluorine gas to thereby form 2'-deoxy-5,6-dihydro-5-fluoro-6-hydroxyuridine, which is a novel compound, and reacting this compound with a carboxylic acid anhydride or halide R--CO--X, where R is an aliphatic group having not more than 20 carbon atoms or a substituted or unsubstituted phenyl group, and X is an acyloxy group RCO.sub.2 or a halogen atom. In the initial fluorination reaction the aqueous solution may contain a carbonate (or a hydrogen carbonate) or a lower fatty acid or its salt to capture hydrogen fluoride formed by the reaction. The next acylating reaction can be promoted by carrying out the reaction in the presence of an organic base such as pyridine.Type: GrantFiled: April 21, 1989Date of Patent: May 7, 1991Assignee: Central Glass Company, LimitedInventors: Yoshiyuki Kikuchi, Akihiro Ishii
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Patent number: 4996318Abstract: The amino-9,10-secosteroids ##STR1## of the present invention contain an amino group attached to the terminal carbon atom of the C.sub.17 -side chain and are useful as pharmaceutical agents for treating a number of conditions including spinal trauma, mild and/or moderate to severe head injury, etc.Type: GrantFiled: September 19, 1989Date of Patent: February 26, 1991Assignee: The Upjohn CompanyInventors: Martin Gall, Robert I. Higuchi
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Patent number: 4988703Abstract: An antiviral compound of the formula: ##STR1## wherein A is selected from a purin-9-yl group, a heterocyclic isostere of a purin-9-yl group, a pyrimidin-1-yl group and a heterocyclic isostere of a pyrimidin-1-yl group; andG and D are independently selected from hydrogen, C.sub.1 to C.sub.10 alkyl and substituted derivatives thereof, --OH, --C(O)H, --CO.sub.2 R.sub.1 l wherein R.sub.1 is hydrogen or C.sub.1 to C.sub.10 alkyl and --OCH.sub.2 PO.sub.3 H.sub.2, with the proviso that one of D or G is other than hydrogen or C.sub.1 to C.sub.10 alkyl; or a pharmaceutically acceptable salt thereof.Type: GrantFiled: May 22, 1989Date of Patent: January 29, 1991Assignee: Abbott LaboratoriesInventors: Daniel W. Norbeck, Terry J. Rosen, Hing L. Sham
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Patent number: 4985066Abstract: A 2-phenoxypyrimidine derivative having the formula: ##STR1## wherein R.sup.1 is a formyl group, a dimethoxymethyl group or --COOR.sup.4 (wherein R.sup.4 is a hydrogen atom, a lower alkyl group, a benzyl group, an alkali metal atom, an alkaline earth metal atom or an organic ammonium group), R.sup.2 is a chlorine atom, a methyl group, a methoxy group or a difluoromethoxy group, R.sup.3 is a methyl group or a methoxy group, X is a halogen atom, a lower alkyl group, a lower alkoxy group, an amino group, a hydroxyl group, a nitro group or a cyano group, and n is 1 or 2.Type: GrantFiled: November 24, 1989Date of Patent: January 15, 1991Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Nobuhide Wada, Yoshihiro Saito, Shoji Kusano, Yasuhumi Toyokawa, Takeshige Miyazawa, Ikuo Kajiwara, Satoru Takahashi
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Patent number: 4973354Abstract: Disclosed are pyrimidine derivatives of the formula (I) and optical isomers thereof and a herbicide containing one or more of them as an active ingredient. ##STR1## where W is O or S; X is a lower alkyl group or a lower alkoxycarbonyl group; R is H, an optionally substituted lower alkyl group, an optionally substituted lower alkenyl group, an optionally substituted lower alkynyl group, an alkyali metal, an alkaline earth metal or an optionally substituted ammonium cation; R.sup.1 and R.sup.2 each are a halogen atom, an optionally substituted lower alkyl group or an optionally substituted lower alkoxy group; n is 3 to 5; m is 0 to 2; and is a single bond or a double bond.Type: GrantFiled: November 28, 1989Date of Patent: November 27, 1990Assignee: Nissan Chemical Industries, Ltd.Inventors: Masataka Hatanaka, Junichi Watanabe, Yasuo Kondo, Koichi Suzuki, Tsutomu Nawamaki, Shigeomi Watanabe
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Patent number: 4970313Abstract: A process for the preparation of optically active 3-de-methylmevalonic acid derivatives, and intermediates A process for the preparation of optically active 3-de-methylmevalonic acid derivatives of the formula I ##STR1## (3,5-dihydroxy carboxylic acid derivatives) or of the formula II ##STR2## (.beta.-hydroxy lactones) in which R, R.sup.1 and Y have the indicated meanings, is described. The invention furthermore relates to aldehydes of the formula XII ##STR3## in which M represents the indicated protective groups. The 3-demethylmevalonic acid derivatives of this invention are useful for lowering cholesterol levels of a host.Type: GrantFiled: December 6, 1988Date of Patent: November 13, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunther Wess, Kurt Kesseler, Ekkehard Baader, Gerhard Beck
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Patent number: 4968340Abstract: A herbicidal alkanoic acid derivative of the formula: ##STR1## wherein R is ##STR2## wherein R.sup.3 is a hydrogen atom, a halogen atom, a halogen-substituted alkyl group, an alkyl group, a cycloalkyl group, an alkylthioalkyl group, a hydroxyalkyl group, a hydroxyl group, a cyano group, an acyloxyalkyl group, a thienyl group, a naphthyl group, a dihydronaphthyl group or ##STR3## wherein R.sup.8 is a hydrogen atom, a halogen atom, a nitro group, an alkyl group, an alkoxy group or --S(O).sub.n R.sup.9 wherein R.sup.9 is an alkyl group, and n is an integer of from 0 to 2, m is an integer of from 0 to 2, each of R.sup.2 and R.sup.4 which may be the same or different is a hydrogen atom or an alkyl group, or R.sup.2 and R.sup.4 form together with the adjacent carbon atom a 3-, 4-, 5- or 6-membered ring which may contain an oxygen atom and may be substituted by one or two alkyl groups, each of R.sup.5 and R.sup.6 which may be the same or different is a hydrogen atom or an alkyl group, R.sup.Type: GrantFiled: June 20, 1989Date of Patent: November 6, 1990Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Koichiro Kaku, Nobuhide Wada, Akira Takeuchi, Yasufumi Toyokawa, Takeshige Miyazawa, Ryo Yoshida, Kazuhiko Sugiyama
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Patent number: 4965357Abstract: The synthesis and application of N(1)-n-alkyl-pyrimidinium-salts are described. These surfactants have a very small critical micelle concentration (CMC) in the order of 10.sup.-5 -10.sup.-7 Mol/Liter. These N(1)-n-alkyl-pyrimidinium components have pharmacological activities and can act as antimetabolites.Type: GrantFiled: August 6, 1987Date of Patent: October 23, 1990Assignee: Medice Chem.-Pharm. Fabrik Putter GmbH & Co. KGInventor: Henrich H. Paradies
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Patent number: 4946495Abstract: A 2-phenoxypyrimidine derivative having the formula: ##STR1## wherein X is a halogen atom or ##STR2## wherein X.sup.1 is a halogen atom, a lower alkyl group or a lower alkoxy group and k is 0, 1 or 2; R.sup.1 is a hydrogen atom, a benzyl group, --(CH.sub.2).sub.m R.sup.3 wherein R.sup.3 is a cyano group, a formyl group, a dialkylamino group, a phenyl group, a pyridyl group, a trimethylsilyl group, a naphthyl group, an alkoxycarbonyl group, a benzoyl group, an alkylthio group, a phenylthio group, an alkylsulfonyl group or a benzyloxy group and m is 1, 2 or 3, or ##STR3## wherein R.sup.4 is a hydrogen atom or a lower alkyl group, R.sup.5 is a lower alkyl group or ##STR4## wherein X.sup.2 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or a nitro group, n is 0 or 1, provided that when R.sup.5 is an alkyl group, n is 1; and R.sup.2 is a chlorine atom or a methoxy group, provided that when R.sup.1 is a hydrogen atom or a benzyl group, X is ##STR5## and R.sup.Type: GrantFiled: April 13, 1988Date of Patent: August 7, 1990Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Nobuhide Wada, Yoshihiro Saito, Shoji Kusano, Yasufumi Toyokawa, Takeshige Miyazawa, Satoru Takahashi, Takayoshi Takehi
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Patent number: 4941909Abstract: The invention is concerned with novel compounds of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 have the significances given in the description, as well as enol ethers and salts thereof and their manufacture, weed control compositions which contain such compounds as active substances and the use of the active substances or compositions for the control of weeds. The invention is also concerned with certain starting materials which have herbicidal activity and with weed control compositions containing these.Type: GrantFiled: February 14, 1989Date of Patent: July 17, 1990Assignee: Hoffmann-La Roche Inc.Inventors: Jean Wenger, Paul Winternitz, Martin Zeller
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Patent number: 4918075Abstract: Antiviral activity is exhibited by compounds having the formula ##STR1## its pharmaceutically acceptable salts thereof wherein R.sub.2 and R.sub.3 are independently hydrogen, --PO.sub.3 H.sub.2 or ##STR2## and R.sub.1 is either a purine, pyrimidine or an analog thereof.Type: GrantFiled: December 20, 1988Date of Patent: April 17, 1990Assignee: E. R. Squibb & Sons, Inc.Inventors: Robert Zahler, Glenn A. Jacobs
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Patent number: 4900352Abstract: A 2-phenoxypyrimidine derivative having the formula: ##STR1## wherein R.sup.1 is a formyl group, a dimethoxymethyl group or --COOR.sup.4 (wherein R.sup.4 is a hydrogen atom, a lower alkyl group, a benzyl group, an alkali metal atom, an alkaline earth metal atom or an organic ammonium group), R.sup.2 is a chlorine atom, a methyl group, a methoxy group or a difluoromethoxy group, R.sup.3 is a methyl group or a methoxy group, X is a halogen atom, a lower alkyl group, a lower alkoxy group, an amino group, a hydroxyl group, a nitro group or a cyano group, and n is 1 or 2.Type: GrantFiled: December 29, 1988Date of Patent: February 13, 1990Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Nobuhide Wada, Yoshihiro Saito, Shoji Kusano, Yasuhumi Toyokawa, Takeshige Miyazawa, Ikuo Kajiwara, Satoru Takahashi
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Patent number: 4871387Abstract: New pyri(mi)dyl-oxy- or -thio-benzoic acid derivatives of the formula ##STR1## are taught which have herbicidal and plant growth regulating activity. In the formula Z can be Ch or N, X is oxygen or sulphur, A is oxygen, sulphur, a radical R.sup.5 --N.dbd.or a radical R.sup.6 O--N.dbd.and B is oxygen, sulphur, a radical ##STR2## with the proviso that at least one of the radicals R.sup.1, R.sup.2 or R.sup.3 represents alkyl or a part of a 3- to 6-membered fused carbocyclic ring.Type: GrantFiled: December 4, 1986Date of Patent: October 3, 1989Assignee: Bayer AktiengesellschaftInventors: Klaus Sasse, Reiner Fischer, Hermann Hagemann, Hans-Joachim Santel, Robert R. Schmidt, Kalus Lurssen
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Patent number: 4870174Abstract: The synthesis of 7-n-alkyl-imidazolium[4,5-d]-pyrimidines, 6-substituted-3n-alkyl-benzimidazolium- and 3n-alkyl-5,6-substituted-benzthiazolium salts are described. There N.sup.+ -surfactants having a substituted heterocycle as a head group have distinguished small critical micelle concentrations (CMC) in the range of 10.sup.-5 -10.sup.-7 Mol/Liter. The size and shape of these micelles in watery solutions are determined by the nature of the anion. The N-surfactants can be used as pharmaceuticals as well as reporter groups in fluorescence studies including immunological assays.Type: GrantFiled: August 6, 1987Date of Patent: September 26, 1989Assignee: Medice chem.-pharm. FabrikInventor: Henrich H. Paradies
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Patent number: 4868187Abstract: Nucleoside analogues having a ring-open structure, of general formula: ##STR1## where R and R' may be hydrogen, silyl groups, substituted alkyl groups, benzyl groups and the like, and X is an optionally substituted base such as guanine or adenine, have been shown to exhibit anti-viral and other biological acivities at non-toxic levels.Type: GrantFiled: March 9, 1987Date of Patent: September 19, 1989Assignee: Syntex (U.S.A.) Inc.Inventor: Kelvin K. Ogilvie
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Patent number: 4863927Abstract: 1-[2-(Hydroxymethyl)cycloalkylmethyl]-5-substituted uracils which are herpes simplex viral thymidine kinase inhibitors, their acyl derivatives, and their pharmaceutically-acceptable salts; pharmaceutical formulations containing these compounds; the treatment of DNA viral, particularly herpes viral, infections with these compounds; methods of preparing these compounds; and novel intermediates useful in their preparation.Type: GrantFiled: May 11, 1987Date of Patent: September 5, 1989Assignee: Merck & Co., Inc.Inventors: Richard L. Tolman, Wallace T. Ashton
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Patent number: 4859229Abstract: The invention is concerned with 3-aryluracils of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are as described herein, as well as salts thereof and their manufacture, weed control compositions which contain such compounds as the active substance and the use of the active substances or compositions for weed control. The invention is also concerned with herbicidally-active starting materials and weed control compositions containing these.Type: GrantFiled: July 21, 1987Date of Patent: August 22, 1989Assignee: Hoffmann-La Roche Inc.Inventors: Jean Wenger, Paul Winternitz
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Patent number: 4845081Abstract: N-methylamino derivatives of biologically active substances which have enhanced delivery across topical membranes and pharmaceutical compositions adapted for topical administration containing same.Type: GrantFiled: September 12, 1986Date of Patent: July 4, 1989Assignee: University of FloridaInventor: Kenneth B. Sloan
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Patent number: 4812164Abstract: The invention is concerned with novel C.sub.1-4 -alkyl, C.sub.2-4 -alkenyl and C.sub.3 or 4 -alkynyl enol ethers of 3-aryluracils of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and X are as defined in the specification, their manufacture, weed control compositions which contain such enol ethers as the active substance and the use of the active substances or compositions for the control of weeds. The invention is also concerned with certain novel intermediates, some of which possess herbicidal activity, and with weed control compositions containing such active substances.Type: GrantFiled: September 15, 1987Date of Patent: March 14, 1989Assignee: Hoffmann-La Roche Inc.Inventors: Jean Wenger, Paul Winternitz
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Patent number: 4810790Abstract: A novel 5-fluorouracil derivative of the formula: ##STR1## wherein R.sup.1 is a fluorine-containing C.sub.1 -C.sub.10 organic group which optionally contains sulfur, oxygen and/or nitrogen. The novel 5-fluorouracil derivative is useful as a carcinostatic substance, which has a high carcinostatic activity but which is less toxicity against digestive tract and causes less autonomic imbalance than other known 5-fluorouracil derivatives.Type: GrantFiled: October 9, 1987Date of Patent: March 7, 1989Assignee: Daikin Industries Ltd.Inventors: Yoshihiro Yamamoto, Kazuhiro Shimokawa, Toru Yoshizawa, Toshihiko Kawano, Hiroyuki Iwai
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Patent number: 4806542Abstract: Isohexide nucleosides of the formula I ##STR1## in which R and B have the meaning given in the description, processes for their preparation and their use as medicaments, in particular as cytostatics, virustatics and immunostimulants.Type: GrantFiled: February 26, 1987Date of Patent: February 21, 1989Assignee: Heinrich Mack Nachf.Inventors: Peter Stoss, Elmar Kaes
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Patent number: 4770691Abstract: As new compounds are provided 2-(4',6'-di-substituted pyrimidine-2'-yl)oxy- or thio-benzoic acid derivatives of the formula ##STR1## wherein R is hydrogen, hydroxy, alkoxy, alkenyloxy, alkylthio or other substituents, R.sup.1 and R.sup.2 are each a halo, alkyl, alkoxy or other substituents; and X is oxygen or sulfur atom. These new compounds are useful as herbicidal agent effective to inhibit the growth of annual weeds and also perennial weeds predominant in irrigated fields of aquatic rice plants and in plowed fields.Type: GrantFiled: October 15, 1986Date of Patent: September 13, 1988Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Yukio Nezu, Kazuhiko Sugiyama, Shoji Kusano, Yasufumi Toyokawa, Takeshige Miyazawa, Ikuo Kajiwara
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Patent number: 4760163Abstract: The disclosure is concerned with novel 3-aryluracils of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and X have the significances given in the description, as well as salts thereof and their manufacture, weed control compositions which contain such compounds as active ingredients and the use of the active ingredients or compositions for the control of weeds. The disclosure also concerns certain herbicidally active starting materials and weed control compositions containing these as active ingredients.Type: GrantFiled: January 25, 1988Date of Patent: July 26, 1988Assignee: Hoffmann-LaRoche Inc.Inventors: Jean Wenger, Paul Winternitz
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Patent number: 4747866Abstract: A pirimidinyloxyalkanamide derivative of Formula 1: ##STR1## wherein R.sub.1 represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkylthio group, a lower alkenylthio group, a lower alkynylthio group, a halogenated lower alkenylthio group, a cycloalkylthio group, an aroxyalkylthio group, a lower alkoxyl group, an amino group, a methanesulfonyl group, a trifluoromethyl group, an anilino group which may be substituted with a halogen atom or a benzylthio group which may be substituted with a halogen atom; R.sub.2 represents a hydrogen atom, a halogen atom, a lower alkyl group, a trifluoromethyl group, an amino group, a lower alkoxy group or a lower alkylthio group; R.sub.3 represents an ethyl group or an n-propyl group; and R.sub.Type: GrantFiled: August 15, 1986Date of Patent: May 31, 1988Assignee: Ube Industries, Ltd.Inventors: Tetsuo Takematsu, Yasutomo Takeuchi, Mitsuaki Takenaka, Seiji Takamura, Hiroshi Hase
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Patent number: 4748245Abstract: A process for the preparation of phenylthiopyrimidines which comprises: (a) reacting a thiopyrimidine; with sulfuryl chloride in the presence of a suitable solvent to form the sulfenyl chloride of said thiopyrimidine; (b) reacting said sulfenyl chloride of said thiopyrimidine with a phenol or substituted phenol, optionally in the presence of a Friedal-Crafts catalyst, to form a thiopyrimidinyl phenol; and (c) reacting said thiopyrimidinylphenol formed in step (b) with a base and an alkylating agent to form the end product.Type: GrantFiled: March 20, 1986Date of Patent: May 31, 1988Assignee: Stauffer Chemical CompanyInventor: Donald R. James
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Patent number: 4748244Abstract: The invention relates to a process for the preparation of pyridine-2,3-dicarboxylic acid derivatives of formula ##STR1## which process comprises reacting a hydrazone of formula II ##STR2## with a maleic acid derivative of formula III ##STR3## to give a 1-amino-1,4-dihydropyridine-2,3-dicarboxylic acid derivative of formula IV ##STR4## and subsequently removing R.sub.9 R.sub.10 NH. In the above formulae, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.9, R.sub.10 and X are as defined in claim 1. The pyridine-2,3-dicarboxylic acid derivatives of formula I are intermediates for the preparation of herbicidal compounds.Type: GrantFiled: May 3, 1985Date of Patent: May 31, 1988Assignee: Ciba-Geigy CorporationInventors: Adrian Waldner, Achim Roloff, Daniel Bellus
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Patent number: 4746352Abstract: The disclosure is concerned with novel 3-aryluracils of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and X have the significances given in the description, as well as salts thereof and their manufacture, weed control compositions which contain such compounds as active ingredients and the use of the active ingredients or compositions for the control of weeds. The disclosure also concerns certain herbicidally active starting materials and weed control compositions containing these as active ingredients.Type: GrantFiled: March 10, 1986Date of Patent: May 24, 1988Assignee: Hoffmann-La Roche Inc.Inventors: Jean Wenger, Paul Winternitz
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Patent number: 4704393Abstract: 5-Fluorouracil derivatives represented by general; formula I: ##STR1## wherein R represents an acyl group derived from an unsaturated higher fatty acid selected from the group consisting of triene higher acids, pentaene higher acids, and hexaene higher fatty acids, can be used as for inhibiting platelet aggregation and an anticancer chemotherapeutic agent. They may be mixed with a pharmaceutically acceptable carrier or a diluent to form a medicinal preparation.Type: GrantFiled: June 17, 1985Date of Patent: November 3, 1987Assignee: Terumo Kabushiki KaishaInventors: Toshio Wakabayashi, Keiko Takahashi, Hajime Katayama
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Patent number: 4692524Abstract: The present invention relates to a process for the preparation of 2-mercapto-4,6-bis-fluoroalkoxypyrimidines of the formula ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.4 alkyl, phenyl or benzyl and each of T.sub.1 and T.sub.2 independently of the other is hydrogen or a --CHX.sub.1 X.sub.2 group, wherein each of X.sub.1 and X.sub.2 independently of the other is trifluoromethyl, fluorine, chlorine or bromine.In accordance with this process, 2-mercapto-4-halo-6-hydroxy-pyrimidines of the formula ##STR2## wherein R.sub.1 is as defined above and Y is chlorine or bromine, are reacted with chlorodifluoromethane or a 1,1-difluoroalkene of the formula ##STR3## wherein each of the X.sub.1 and X.sub.2 independently of the other is trifluoromethyl, fluorine, chlorine or bromine, in an inert solvent and in the presence of a strong base, to give a 2-mercapto-4-halo-6-fluoro-alkoxypyrimidine of the formula ##STR4## wherein R.sub.1, Y and T.sub.Type: GrantFiled: May 2, 1986Date of Patent: September 8, 1987Assignee: Ciba-Geigy CorporationInventor: Robert Hassig
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Patent number: 4666627Abstract: Novel 4-heterocyclylvinyl-4'-styryl-biphenyls of the formula ##STR1## are described, i which A is an isoxazolyl, oxadiazolyl, pyrimidinyl or triazinyl radical which is unsubstituted or substituted by a non-chromophoric substituent, R.sub.1 is hydrogen or a non-chromophoric substituent and R.sub.2 is hydrogen, halogen, or alkyl; processes for the preparation of these compounds are also described.The novel 4-heterocyclylvinyl-4'-styryl-biphenyls can be used as fluorescent brighteners for high-molecular organic materials, in particular materials of polyamide and polyester, especially for polyester textiles.Type: GrantFiled: July 27, 1984Date of Patent: May 19, 1987Assignee: Ciba-Geigy CorporationInventor: Hans R. Meyer
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Patent number: 4659827Abstract: 2,4-Dihydroxypyrimidines of the formula ##STR1## with the substituent meanings given in the description, are obtained by reacting pyrimidines of the formula ##STR2## with the substituent meanings given in the description, with aqueous alkalis at elevated temperature. 2,4,5,6-Tetrachloropyrimidine is obtained from the dihydroxypyrimidines by reaction with agents which replace hydroxyl by chlorine.Type: GrantFiled: November 6, 1985Date of Patent: April 21, 1987Assignee: Bayer AktiengesellschaftInventors: Karl J. Herd, Karl H. Schundehutte
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Patent number: 4631342Abstract: A process for producing 5-fluorouracil using an aqueous phosphoric acid solution as a solvent which is a good solvent for an intermediate resulting from the reaction between uracil and elemental fluorine, and permits the reaction to proceed smoothly, but which can precipitate the final product, 5-fluorouracil, after cooling the heat-treated reaction solution to room temperature, with no need to evaporate the solvent.The process comprises reacting uracil in an aqueous phosphoric acid solution with elemental fluorine and heating the resultant reaction solution to form 5-fluorouracil.Type: GrantFiled: March 7, 1985Date of Patent: December 23, 1986Assignees: Onoda Cement Company, Ltd., Sagami Chemical Research CenterInventors: Teruo Umemoto, Eiji Ogura
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Patent number: 4605738Abstract: Highly selective and high yield process for producing antitumor agent 1-phthalidyl-5-fluorouracil derivatives of formula (I) which comprises reacting a phthalidyl compound (II) with an amine (III) to yield the quaternary ammonium salts (IV), and reacting the latter with 5-fluorouracil. ##STR1## [wherein X is leaving group; ##STR2## is triethylamine, N-methylmorpholine, N-ethylmorpholine, and the like; R.sup.4 and R.sup.5 each is hydrogen, trialkylsilyloxy, alkoxy, nitro, cyano, carboxy, or alkoxycarbonyl].Type: GrantFiled: November 9, 1983Date of Patent: August 12, 1986Assignee: Shionogi & Co., Ltd.Inventors: Susumu Kamata, Nobuhiro Haga, Wataru Nagata, Takeaki Matsui
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Patent number: 4605659Abstract: Novel 4-substituted-5-hydroxymethyl-1,2-cyclopentanediols or 1-cyclopentanol substituted at the 3-position by various heterocyclic groups are useful as antiviral agents.Type: GrantFiled: April 30, 1985Date of Patent: August 12, 1986Assignee: Syntex (U.S.A.) Inc.Inventors: Julien P. H. Verheyden, John C. Martin, G. V. Bindu Madhaven, Daniel P. C. McGee, Ernest J. Prisbe
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Patent number: 4596869Abstract: A novel compound, useful as an intermediate in the production of compounds of high antimicrobial activity, of the formula: ##STR1## wherein R.sub.a.sup.1 is hydrogen, amino or a protected amino group,R.sub.b.sup.1 and R.sub.c.sup.1 are each hydrogen, halogen, lower alkoxy or arylthio,R.sup.14 is carboxy or a protected carboxy group,X is lower alkylene or a group of the formula: ##STR2## in which R.sup.6 is hydrogen or an organic residue which may have suitable substituent(s), andZ is N or CH,or a salt thereof.Type: GrantFiled: September 19, 1985Date of Patent: June 24, 1986Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takashi Kamiya, Tsutomu Teraji, Yoshiharu Nakai, Kazuo Sakane, Jiro Goto
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Patent number: 4590189Abstract: The compound of the formula ##STR1## wherein X is a cyclic group which may optionally be substituted; Y is a carboxyl group which may optionally be esterified or amidated; Z is --CH.dbd.CH--CH.dbd.CH--, --S--(CH.sub.2).sub.l --S--(l is an integer of 1 to 3), --N.dbd.CH--CH.dbd.N-- or --(CH.sub.2).sub.m --(m is an integer of 3 to 5); ring A may optionally be substituted with halogen, nitro, amino, alkanoylamino, alkoxycarbonyl, carboxyl or carbamoyl; and n is an integer of 1 to 3, and salts thereof. The compounds display a strong antianxiety effect to mammalian animals and are useful for the prevention or treatment of a disease such as psychosomatic disease and anxiety neurosis.Type: GrantFiled: March 24, 1983Date of Patent: May 20, 1986Assignee: Takeda Chemical Industries, Ltd.Inventors: Kentaro Hiraga, Yoshiaki Saji
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Patent number: 4567260Abstract: A new synthesis of 5-deazariboflavine is afforded by condensing N-D-ribityl-3,4-xylidine with a novel chemical intermediate, 6-chloro-5-formyluracil.Type: GrantFiled: June 30, 1983Date of Patent: January 28, 1986Assignee: Toyo Jozo Kabushiki KaishaInventor: Fumio Yoneda
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Patent number: 4532240Abstract: Substituted-phenyl derivatives of 5-(1,4-piperazinyl)-2,4-pyrimidinediamine are effective as antibacterial and antitumor agents. Methods of preparing such compounds, pharmaceutical compositions based thereon, and a method of treating bacterial infections in a mammal in need of such treatment are disclosed.Type: GrantFiled: August 9, 1983Date of Patent: July 30, 1985Assignee: Warner-Lambert CompanyInventors: Leslie M. Werbel, Jocelyn H. Hung
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Patent number: 4473570Abstract: Imidazo[1,5-c]pyrimidin-5-ones have been found to have potent bronchodilator activity. Pharmacological methods of using these compounds and pharmaceutical compositions containing these compounds are also disclosed.Type: GrantFiled: August 2, 1983Date of Patent: September 25, 1984Assignee: Riker Laboratories, Inc.Inventor: James J. Wade
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Patent number: 4466916Abstract: Novel polysubstituted 2-keto-1,4-diazacycloalkanes are powerful stabilizers for materials subject to ultraviolet (UV) light degradation, particularly for polyolefins. The cyclic 2-keto compounds of this invention have (a) a fixed two-carbon bridge between the N.sup.1 and N.sup.4 atoms of the diaza ring, the remaining portion of the ring having a variable length bridge of two or more carbon atoms, (b) and N-adjacent carbonyl in the fixed two-carbon bridge, and (c) at least one N.sup.4 -adjacent carbon atom of the diaza ring is polysubstituted, that is, has two substituents which may be cyclizable.Compositions containing (a) the polysubstituted 2-keto-1,4-diazacycloalkanes of this invention, and (b) prior art polysubstituted 2-keto-1,4-diazacycloalkanes, exhibit excellent stability to UV light.Type: GrantFiled: June 17, 1982Date of Patent: August 21, 1984Assignee: The B. F. Goodrich CompanyInventors: John T. Lai, Pyong N. Son
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Patent number: 4455424Abstract: The present invention relates to naphthoquinone derivatives of formula I, ##STR1## in which R.sub.1 signifies a halogen atom, a nitro group or an unsubstituted or substituted alkoxy or amino group,R.sub.2 signifies the atoms necessary to form an unsaturated ring system, which ring system has 1 or 2 nuclei and is unsubstituted or substituted,R.sub.3 signifies an unsubstituted or substituted s-triazinyl or pyrimidyl radical, andn is 0, 1 or 2,which compounds are free from sulphonic acid groups are useful as pigments or disperse dyes.Type: GrantFiled: February 24, 1977Date of Patent: June 19, 1984Assignee: Sandoz Ltd.Inventor: Bansi L. Kaul
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Patent number: 4438267Abstract: Novel 2,4-diamino-5-(substituted naphthylmethyl)pyrimidines have been found to have superior antibacterial activity.Type: GrantFiled: November 9, 1981Date of Patent: March 20, 1984Inventors: Susan M. Daluge, Paul M. Skonezny
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Patent number: 4427437Abstract: A process of inhibiting the growth of, severely damaging, or killing plants which process comprises applying to the plant or to the growth medium thereof an effective amount of a composition comprising as active ingredient a compound of formula I: ##STR1## wherein A, B and D are independently chosen from the group consisting of hydrogen, halogen, hydroxy, nitro, cyano, thiocyano, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted alkenyloxy, optionally substituted alkynyloxy, optionally substituted alkylthio, optionally substituted cycloalkyl, optionally substituted amino, optionally substituted phenyl, carboxy, alkoxycarbonyl, optionally substituted carbamoyl, sulfo, alkylsulfonyl and optionally substituted sulfamoyl; R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.Type: GrantFiled: September 5, 1978Date of Patent: January 24, 1984Assignee: ICI Australia LimitedInventors: Alexander Serban, Keith G. Watson, Richard B. Warner
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Patent number: 4415573Abstract: Novel uracil derivatives of the formula ##STR1## (wherein R.sub.1, R.sub.2 R.sub.3 and X are defined in the description) and their pharmaceutically acceptable salts, process for preparing the same and pharmaceutical composition containing the same are disclosed. The uracil derivatives have good antitumor activity and, therefore, are useful as antitumor preparation.Type: GrantFiled: August 10, 1981Date of Patent: November 15, 1983Assignee: Chugai Seiyaku Kabushiki KaishaInventors: Kiyoshige Ochi, Katsuhito Miyamoto, Hiroki Mitsui, Yumiko Tsuruma, Isao Matsunaga, Takashi Matsuno, Shigeru Takanashi, Minoru Shindo