Benzothiazoles (including Hydrogenated) Patents (Class 544/135)
-
Patent number: 4696939Abstract: Compounds of the formula ##STR1## and their pharmaceutically acceptable salts, wherein the substituents are as defined herein, having antihypertensive activity.Type: GrantFiled: November 29, 1985Date of Patent: September 29, 1987Assignee: USV Pharmaceutical CorporationInventors: John T. Suh, John J. Piwinski, Howard Jones, Edward S. Neiss
-
Patent number: 4692445Abstract: A class of bicyclic benzenoid aminoalkylene ether and thioether compounds exhibiting pharmacological activity, including anti-secretory and anti-ulcerogenic activity, pharmaceutical compositions comprising these compounds, and methods for the treatment of gastrointestinal hyperacidity and ulcerogenic disorders in mammals using said compositions.Type: GrantFiled: November 12, 1986Date of Patent: September 8, 1987Assignee: Rorer Pharmaceutical CorporationInventors: Donald E. Kuhla, Henry F. Campbell, William L. Studt
-
Patent number: 4670556Abstract: This invention relates to a process for the production of benzothiazolyl sulphenamides corresponding to the following general formula: ##STR1## in which a corresponding 2-mercaptobenzothiazole or a dibenzothiazolyl-2,2'-disulphide is reacted with a primary or secondary amine at temperatures of from 0 to 100.degree. C. in the presence of ammonia, oxygen, a copper-containing catalyst and a reaction medium containing an excess of the primary or secondary amine or of a mixture of that amine with water and/or a water-miscible organic solvent.Benzothiazolyl sulphenamides are valuable vulcanization accelerators.Type: GrantFiled: July 6, 1984Date of Patent: June 2, 1987Assignee: AKZO NVInventors: Hans Zengel, Ludwig Eisenhuth, Manfred Bergfeld
-
Patent number: 4621142Abstract: A process for preparing certain benzo- and thieno-fused heterocyclic compounds having H.sub.2 -receptor antagonist and antisecretory activity, which comprises the amide reduction of N-substituted carbamoyl-containing benzo- or thieno-fused heterocyclic intermediates; and said N-substituted carbamoyl-containing benzo- or thieno-fused heterocyclic intermediates.Type: GrantFiled: July 30, 1985Date of Patent: November 4, 1986Assignee: American Home Products CorporationInventors: Anthony C. Scotese, Arthur A. Santilli, Donald P. Strike
-
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
-
Patent number: 4590192Abstract: Compounds of formula (I), or a pharmaceutically acceptable salt, quaternized derivative, N-oxide or solvate thereof:R.sub.1 --Ar--(CH.sub.2).sub.a --X--(CH.sub.2).sub.b --NH--Het (I)wherein: the substituents are defined in the specification.The compounds are useful in treating excess gastric acid secretions such as peptic ulcers.Type: GrantFiled: September 29, 1983Date of Patent: May 20, 1986Assignee: Beecham Group p.l.c.Inventors: Charles S. Fake, Gordon Burrell
-
Patent number: 4589991Abstract: There is disclosed a process for the solubilization of a mercaptobenzothiazole amine salt with a solvent such as dihexyl phthalate which solubilized salt is in turn suitable for dissolution into a lubricating oil composition, such as an automatic transmission fluid, even at room temperature.Type: GrantFiled: July 1, 1985Date of Patent: May 20, 1986Assignee: Exxon Research & Engineering Co.Inventors: Jack Ryer, Chung Kun Shih, John E. Williams
-
Patent number: 4589910Abstract: A 4'-(Benzisothiazol-5-yloxy)-phenylureas of the formula ##STR1## where R.sup.1 and R.sup.2 are each a saturated straight-chain or branched aliphatic radical of 1 to 10 carbon atoms, an unsaturated straight-chain or branched aliphatic radical of 3 to 10 carbon atoms, or an araliphatic or aromatic radical which may be substituted by 1, 2 or 3 C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, cyano, halogen, nitro, monofluoromethyl or trifluoromethyl groups, or are each alkoxy of 1 to 6 carbon atoms, R.sup.2 may furthermore be hydrogen, or R.sup.1 and R.sup.2, together with the nitrogen atom, may be members of a 5-membered or 6-membered ring which may contain further nitrogen and/or oxygen atoms as heteroatoms, and X is hydrogen, trifluoromethyl or chlorine, processes for their preparation, and herbicides containing ureas of the formula I as active ingredients.Type: GrantFiled: April 30, 1985Date of Patent: May 20, 1986Assignee: BASF AktiengesellschaftInventors: Helmut Hagen, Hans Ziegler, Bruno Wuerzer
-
Patent number: 4558125Abstract: The invention relates to benzothiazoline derivatives of the formula [I] and salts thereof, which are useful for (i) treating cardiovascular diseases, and (ii) as the active ingredient of pharmaceutical compositions. Formula [I] follows: ##STR1## wherein R.sup.1 is lower alkanoyl;R.sup.2 is one or more group(s) selected from hydrogen, lower alkyl, lower alkoxy, hydroxy, halogen, nitro, halogenolower alkyl and sulfamoyl;R.sup.3 is --COR.sup.8 ;R.sup.8 is hydroxy, lower alkoxy, ##STR2## Z is straight or branched alkylene containing 1 to 6 carbon atoms; m is 0 or 1; n is 0 or 1; and p is 4 or 5.Type: GrantFiled: May 21, 1984Date of Patent: December 10, 1985Assignee: Santen Pharmaceutical Co., Ltd.Inventors: Jun-ichi Iwao, Tadashi Iso, Masayuki Oya
-
Patent number: 4552969Abstract: The invention relates to benzothiazoline derivatives of the formula [I] and salts thereof, which are useful for (i) treating cardiovascular diseases, and (ii) as the active ingredient of pharmaceutical compositions. Formula [I] follows: ##STR1## wherein R.sup.1 is lower alkanoyl;R.sup.2 is one or more group(s) selected from hydrogen, lower alkyl, lower alkoxy, hydroxy, halogen, nitro, halogenolower alkyl and sulfamoyl;R.sup.3 is ##STR2## R.sup.4 and R.sup.5 each is hydrogen, lower alkyl, cyclohexyl or substituted lower alkyl;Z is straight or branched alkylene containing 1 to 6 carbon atoms;m is 0 or 1; n is 0 or 1; and p is 4 or 5.Type: GrantFiled: May 21, 1984Date of Patent: November 12, 1985Assignee: Santen Pharmaceutical Co., Ltd.Inventors: Jun-ichi Iwao, Tadashi Iso, Masayuki Oya
-
Patent number: 4532062Abstract: There are disclosed improved additives for power shift transmission fluids being amine or ammonium salts of mercaptobenzothiazole dissolved in excess amine. The additives are useful as corrosion inhibitors, anti-oxidants and friction modifiers.Type: GrantFiled: January 23, 1984Date of Patent: July 30, 1985Assignee: Exxon Research & Engineering Co.Inventors: Jack Ryer, Ricardo Bloch, Harold E. Deen
-
Patent number: 4528375Abstract: Histamine H.sub.2 -receptor antagonists of the formula ##STR1## wherein A, m, Z, n and R.sup.Type: GrantFiled: April 16, 1984Date of Patent: July 9, 1985Assignee: Bristol-Myers CompanyInventors: Ronnie R. Crenshaw, Aldo A. Algieri
-
Patent number: 4528378Abstract: Histamine H.sub.2 -receptor antagonists of the formula ##STR1## wherein A, m, Z, n and R.sup.Type: GrantFiled: April 16, 1984Date of Patent: July 9, 1985Assignee: Bristol-Myers CompanyInventors: Ronnie R. Crenshaw, Aldo A. Algieri
-
Patent number: 4505923Abstract: Novel ethers of hydroxy-2-benzothiazolesulfonamide are useful for the topical treatment of elevated intraocular pressure. Ophthalmic compositions include drops and inserts.Type: GrantFiled: October 31, 1983Date of Patent: March 19, 1985Assignee: Merck & Co., Inc.Inventors: Jacob M. Hoffman, Jr., Otto W. Woltersdorf, Jr.
-
Patent number: 4499103Abstract: Novel 2-benzothiazolesulfonamides are useful for the topical treatment of elevated intraocular pressure. Ophthalmic compositions including drops and inserts are also disclosed, as well as methods for preparing the novel compounds.Type: GrantFiled: March 17, 1983Date of Patent: February 12, 1985Assignee: Merck & Co., Inc.Inventor: S. Jane de Solms
-
Patent number: 4490527Abstract: Compounds of the formula: ##STR1## wherein B is a moiety having the formula: ##STR2## R is mono- or dihalo, amino, nitro, cyano, hydroxy, trifluoromethyl, mercapto, lower alkyl, lower alkoxy, alkanoyl, cycloalkyl of 4-7 carbon atoms, carboxy, alkoxycarbonyl, mono- or di-lower alkyl substituted amino, alkanoylamino, lower alkyl thio, lower alkylsulfonyl, sulfamoyl, lower alkyl substituted sulfamoyl, phenyl or phenyl substituted with halo, lower alkyl, lower alkoxy, trifluoromethyl, hydroxy, amino, cyano or nitro.X is SO.sub.2, SO, S or C.dbd.O; andA is amine selected from the group ##STR3## , wherein R.sup.1 is hydrogen or R.sup.2 CH.sub.2 wherein R.sup.2 is mono- or diloweralkylamino, mono- or di-N-lower alkylaminoloweralkyl, (2-furyl)methylamino, benzylamino, lowercycloalkylamino, 1-pyrrolidinyl, 1-piperidinyl, 1-hexahydroazepinyl, 1-octahydroazocinyl, 3-thiazolidinyl, 4-morpholinyl or 4-thiomorpholinyl; R.sup.3 is hydrogen or (1-piperidinyl)methyl with the proviso that when R.sup.Type: GrantFiled: February 22, 1983Date of Patent: December 25, 1984Assignee: American Home Products CorporationInventors: Guy A. Schiehser, Donald P. Strike
-
Patent number: 4479949Abstract: This invention relates to benzothiazoline derivatives of the formula [I] and salts thereof, which are useful for (i) treating cardiovascular diseases, and (ii) as the active ingredient of pharmaceutical compositions. Formula [I] follows: ##STR1## wherein R.sup.1 is lower alkanoyl;R.sup.2 is one or more group(s) selected from hydrogen, lower alkyl, lower alkoxy, hydroxy, halogen, nitro, halogeno-lower alkyl and sulfamoyl;R.sup.3 is ##STR2## R.sup.6 is hydrogen, alkyl, substituted alkyl, alkanoyl, substituted alkanoyl, alkenoyl, substituted alkenoyl or furylcarbonyl;R.sup.7 is hydrogen, hydroxy, phenyl-lower alkyl or banzoyl;Z is strainght or branched alkylene containing 1 to 6 carbon atoms;m is 0 or 1; n is 0 or 1; and p is 5.Type: GrantFiled: April 14, 1983Date of Patent: October 30, 1984Assignee: Santen Pharmaceutical Co., Ltd.Inventors: Jun-ichi Iwao, Tadashi Iso, Masayuki Oya
-
Patent number: 4474965Abstract: This disclosure relates to 3-substituted aminoalkyl-2-benzothiazolinones which are useful as plant growth regulants. More specifically, this disclosure relates to 3-substituted aminoalkyl-2-benzothiazolinones and compositions containing said compounds and to the use of said compounds and compositions to regulate the growth of leguminous plants such as soybeans.Type: GrantFiled: September 1, 1982Date of Patent: October 2, 1984Assignee: Monsanto CompanyInventor: John J. D'Amico
-
Patent number: 4472417Abstract: Novel carbamates of 6(or 5)-hydroxy-2- benzothiazolesulfonamide are useful for the topical treatment of elevated intraocular pressure. Ophthalmic compositions include drops and inserts.Type: GrantFiled: April 22, 1983Date of Patent: September 18, 1984Assignee: Merck & Co., Inc.Inventor: Otto W. Woltersdorf, Jr.
-
Patent number: 4472418Abstract: Novel sulfamates of 6(or 5)-hydroxy-2-benzothiazolesulfonamide are useful for the topical treatment of elevated intraocular pressure. Ophthalmic compositions include drops and inserts.Type: GrantFiled: April 22, 1983Date of Patent: September 18, 1984Assignee: Merck & Co., Inc.Inventor: Otto W. Woltersdorf, Jr.
-
Patent number: 4470991Abstract: Novel sulfonates of 6(or 5)-hydroxy-2-benzothiazolesulfonamide are useful for the topical treatment of elevated intraocular pressure. Ophthalmic compositions include drops and inserts.Type: GrantFiled: April 22, 1983Date of Patent: September 11, 1984Assignee: Merck & Co., Inc.Inventor: Otto W. Woltersdorf, Jr.
-
Patent number: 4461897Abstract: Benzothiazole-2-sulfenamides are prepared by reacting a 2-mercaptobenzothiazole and a primary or secondary amine with oxygen in the presence of a catalyst, for example a metal phthalocyanine, in a reaction medium consisting of (i) a mixture of the amine and water in which the amount of water at the outset of the reaction is from 0.2 to 20% by weight of the mixture, or (ii) a mixture as defined in (i) diluted with an inert organic solvent miscible with the mixture, in a proportion of up to two parts by weight of the inert organic solvent per part by weight of the mixture.Type: GrantFiled: September 24, 1982Date of Patent: July 24, 1984Assignee: Monsanto Europe S.A.Inventors: Alec S. Cobb, David J. Williams
-
Patent number: 4418030Abstract: The organic substance present in the form of a melt is cooled below its solidification point in a twin-screw extruder so that it crystallizes out. The crystallized material is then extruded through a breaker plate at the end of the screw extruder and further cooled. It is essential that the temperature prevailing in the screw extruder, its rotational speed and the temperature of the breaker plate should be adjusted such that from 70% to 99.5% and preferably from 95 to 99.5% of the material has solidified by the time it reaches the end of the screw, the non-crystallized liquid residue only crystallizing out during the subsequent cooling operation. Accordingly, a small residue of melt is present during extrusion through the breaker plate. In addition, extrusion is facilitated if the breaker plate is kept at a temperature in the vicinity of the melting point of the material in question.Type: GrantFiled: December 15, 1981Date of Patent: November 29, 1983Assignee: Bayer AktiengesellschaftInventors: Ernst-Willi Muller, Claus Rathjen
-
Patent number: 4409216Abstract: A compound, with hypoglycaemic activity, having formula (II) or a pharmaceutically acceptable acid addition salt thereof: ##STR1## wherein X represents oxygen or sulphur;R.sup.1 R.sup.2 are the same or different and represent hydrogen, halogen, C.sub.1-6 alkyl, phenyl, benzyl,C.sub.3-6 cycloalkyl, carbo-C.sub.1-6 alkoxy or C.sub.1-6 carboxy or R.sup.1 and R.sup.2 represent the remaining members of a benzene ring;R.sup.3 represents hydrogen, C.sub.1-6 alkyl, phenyl or benzyl;R.sup.4 represents hydrogen or C.sub.1-6 alkyl;R.sup.5 represents C.sub.1-6 alkyl, phenyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl, and C.sub.1-6 alkoxy; or benzyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl and C.sub.1-6 alkoxy; or R.sup.4 and R.sup.5 together represent the remaining members of a 5- or 6- membered ring optionally containing an oxygen, sulphur or additional nitrogen atom and being optionally substituted with C.sub.1-6 alkyl; andR.sup.Type: GrantFiled: April 11, 1980Date of Patent: October 11, 1983Assignee: Beecham Group LimitedInventor: Barrie C. C. Cantello
-
Patent number: 4383850Abstract: Compounds of the formula ##STR1## in which R denotes halogen, CF.sub.3, NO.sub.2 or CN, n denotes 0-2, X denotes O or S and Z denotes radicals of the formulae ##STR2## or --C.sub.p H.sub.2p --R.sub.3 (in which, inter alia, R.sub.3 can be a heterocyclic radical), are valuable herbicides, particularly against monocotyledonous weeds.Type: GrantFiled: April 13, 1982Date of Patent: May 17, 1983Assignee: Hoechst AktiengesellschaftInventors: Reinhard Handte, Klaus Bauer, Hermann Bieringer
-
Patent number: 4371734Abstract: A process for the preparation of a thiazole derivative of the formula ##STR1## where R.sup.1 to R.sup.4 are organic radicals and R.sup.3 and R.sup.4 may also be hydrogen, by reacting a compound of the formula ##STR2## with a methylene-active compound of the formula ##STR3## in the presence of a base, and the thiazole derivative thus obtained.Type: GrantFiled: May 1, 1980Date of Patent: February 1, 1983Assignee: BASF AktiengesellschaftInventor: Guenther Seybold
-
Patent number: 4359574Abstract: In one aspect, this invention relates to a method of synthesizing certain 3-(4'-OH-carbocyclic aryl)-3-(carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxides (and -2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxides) by reacting a 3-(4'-OP-carbocyclic aryl)-3-(carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxide (or a 3-(4'-OP-carbocyclic aryl)-3-(carbocyclic aryl)-2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxide) wherein P is a protecting group with a carboxylic acid halide in pyridine to yield the corresponding 2-carbonyl derivative followed by removing the protecting group with weak acid to give the product. Optionally, the acylation step may be carried out by sequentially reacting the starting compound with an alkali metal hydride to give the corresponding 2-alkali metal salt and then reacting with the carboxylic acid halide in a suitable inert organic solvent.Type: GrantFiled: August 4, 1980Date of Patent: November 16, 1982Assignee: Polaroid CorporationInventors: Stanley M. Bloom, Alan L. Borror, James W. Foley
-
Patent number: 4344946Abstract: Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.1 ', which may be identical to or different from each other, are each hydrogen or alkyl of 1 to 2 carbon atoms;R.sub.2 and R.sub.2 ', which may be identical to or different from each other, are each hydrogen or ##STR2## but other than both hydrogen at the same time, where A is alkylene of 1 to 2 carbon atoms,R.sub.5 is hydrogen, lower alkyl, lower alkylamino-lower alkyl, lower alkoxy-lower alkyl, hydroxycarbonyl-lower alkyl, cycloalkyl of 5 to 8 carbon atoms, lower alkyl-cycloalkyl of 5 to 8 carbon atoms, phenyl or morpholino;R.sub.6 is hydrogen, lower alkyl, lower alkylamino-lower alkyl or lower alkoxy-lower alkyl; orR.sub.5 and R.sub.Type: GrantFiled: August 28, 1980Date of Patent: August 17, 1982Assignee: Boehringer Ingelheim GmbHInventors: Ernest Cullen, Genus Possanza, Patrick B. Stewart
-
Patent number: 4323677Abstract: N-amides of 2-benzothiazolinone have been found to be effective in regulating the growth of leguminous plants.Type: GrantFiled: June 25, 1979Date of Patent: April 6, 1982Assignee: Monsanto CompanyInventor: John J. D'Amico
-
Patent number: 4311839Abstract: In one aspect, this invention relates to a method of synthesizing certain 3-(4'-OP-carbocyclic aryl)-3-(carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxides (and -2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxides) by reacting (a) a 3-(4'-OP-carbocyclic aryl)-benz[d]isothiazole-1,1-dioxide wherein P is a protecting group or a 3-(4'-OP-carbocyclic aryl)-naphtho[1,8-de]-1,2-thiazine-1,1-dioxide wherein P is a protecting group and (b) a carbocyclic aryllithium compound to give (c) the corresponding 3-(4'-OP-carbocyclic aryl)-3-(carbocyclic aryl)-2,3-dihydrobenz[d]-isothiazole-1,1-dioxide or the corresponding 3-(4'-OP-carbocyclic aryl)-3-(carbocyclic aryl)-2,3-dihydronaphtho-[1,8-de]-1,2-thiazine-1,1-dioxide.Type: GrantFiled: December 22, 1980Date of Patent: January 19, 1982Assignee: Polaroid CorporationInventors: Alan L. Borror, Louis Cincotta, James W. Foley, Marcis M. Kampe
-
Patent number: 4299959Abstract: A fluorescent pigment consisting of N-substituted iminocoumarins of the general formula I, ##STR1## wherein X.sub.1 is a cyano group, a carboxamido group or an aryl or a heteroaryl radical linked directly or through a --CO or --SO.sub.2 group,X.sub.2 is an amino group, hydroxy group or an alkoxy group and when it is an amino group, may carry an optionally substituted alkylene or alkylidene group bound in ortho position to the nitrogen atom and in para position with respect to the coumarin oxygen atom,X.sub.3 is a hydrogen atom, a halogen atom or a cyano group andX.sub.4 is a functionally converted carboxyl groups. The new dyestuffs dye polyester fiber in orange or red shades with good fastness.Type: GrantFiled: January 31, 1979Date of Patent: November 10, 1981Assignee: Ciba-Geigy CorporationInventor: Nalin B. Desai
-
Patent number: 4293462Abstract: The invention concerns a process for the manufacture of 7.beta.-amino-3-cephem-3-ol-4-carboxylic acid compounds by ring closure of esters of 2-[4-(substituted-thio)-3-acylamino-2-oxoazetidin-1-yl]-3-substituted-amin o-crotonic acids and solvolyzing the enamino group in the resulting 7.beta.-acylamino-3-substituted-amino-cephem-4-carboxylic acid esters.Type: GrantFiled: December 10, 1979Date of Patent: October 6, 1981Assignee: Ciba-Geigy CorporationInventors: Robert B. Woodward, Hans Bickel
-
Patent number: 4283538Abstract: In one embodiment, the present invention is concerned with novel triarylmethane compounds possessing in their triaryl structure a 4'-oxo-1'-naphthylidene (or a 4'-oxo-1'-phenylidene) moiety and a phenyl moiety substituted in the ortho-position to the central carbon atom with the group ##STR1## wherein R is an alkyl group or a phenyl group, unsubstituted or substituted with a solubilizing group; R' is selected from ##STR2## wherein R" is methyl, unsubstituted or substituted with one or two halo groups or substituted with a phenyl, alkoxy or phenoxy group and ##STR3## wherein Y is an electron-withdrawing group; and R and R' taken with said ##STR4## represents ##STR5## In another embodiment the present invention is concerned with a method of synthesizing the aforementioned compounds by reacting, e.g., a 2-R'-3-(4'-hydroxy-1'-phenyl/naphthyl)-3-(phenyl/naphthyl)-2,3-dihydrobenz [d]isothiazole-1,1-dioxide with an alkylation reagent in the presence of base.Type: GrantFiled: December 26, 1979Date of Patent: August 11, 1981Assignee: Polaroid CorporationInventor: James W. Foley
-
Patent number: 4283537Abstract: In one embodiment, the present invention is concerned with 3,3-disubstituted sulfam(na)phthaleins wherein one of the 3-substituents is derived from a perhalomethylcarbinol-substituted phenol or 1-naphthol useful as intermediates in the preparation of certain N-acylated sulfam(na)phthalein compounds, which compounds find utility, e.g., as pH-sensitive indicator dyes or photographic light-screening dyes.In another embodiment, the present invention is concerned with a method of synthesizing said sulfam(na)phthalein intermediates by reacting certain 3-substituted-benz[d]isothiazole-1,1-dioxides (or 3-substituted-naphtho[1,8-de]-1,2-thiazine-1,1-dioxides) and a 4-OLi-naphthyllithium compound or a 4-OLi-phenyllithium compound substituted in the 3-position with a lithiated perhalomethylcarbinol group.Type: GrantFiled: November 2, 1978Date of Patent: August 11, 1981Assignee: Polaroid CorporationInventors: Louis Cincotta, James W. Foley
-
Patent number: 4259493Abstract: The present invention is concerned with novel 3,3-disubstituted-sulfam(na)phthaleins wherein one of the 3-substituents is derived from a 1-naphthol or a phenol substituted in the 2-position with a perhalomethylcarbinol group and wherein the N atom of the sulfam(na)phthalein ring is substituted with ##STR1## wherein R is alkyl or aryl or with ##STR2## wherein Y is hydrogen or an electron-withdrawing group, which compounds find utility, e.g., as pH-sensitive indicator dyes or as photographic light-screening dyes.Type: GrantFiled: November 2, 1978Date of Patent: March 31, 1981Assignee: Polaroid CorporationInventor: James W. Foley
-
Patent number: 4256744Abstract: This invention relates to novel compounds of the general formula (I): ##STR1## wherein A represents ##STR2## in which B represents a ring-forming residue of a 5- or 6-membered carbon-containing heterocycling ring containing at least one nitrogen atom and which may further contain an oxygen atom in the ring, and R.sub.1 and R.sub.Type: GrantFiled: February 2, 1979Date of Patent: March 17, 1981Assignee: Meiji Seika Kaisha, Ltd.Inventors: Shigeo Seki, Yashuharu Sekizawa, Fumio Kai, Yukio Suzuki, Michiaki Iwata, Tetsuro Watanabe
-
Patent number: 4255578Abstract: The present invention is concerned with a method of synthesizing certain ##STR1## 3-disubstituted sulfam(na)phthalein compounds useful as pH-sensitive indicator dyes and with intermediates useful in the preparation of said compounds. The subject method comprises (1) reacting (a) a 3,3-disubstituted sulfam(na)phthalein wherein one of the 3-substituents is a 4'-hydroxy-1'-phenyl moiety or a 4'-hydroxy-1'-naphthyl moiety substituted in the 3'-position with a perhalomethylcarbinol group and (b) an acid halide, ##STR2## wherein R is alkyl or aryl to give (c) an acylated intermediate wherein the N atom of the sulfam(na)phthalein ring and the 4'-hydroxy and carbinol hydroxy groups are acylated with ##STR3## and (2) treating said compound (c) with alkali to selectively remove said ##STR4## from said hydroxy groups and yield the ##STR5## product. The intermediates of the present invention are the acylated compounds (c).Type: GrantFiled: November 2, 1978Date of Patent: March 10, 1981Assignee: Polaroid CorporationInventors: Louis Cincotta, James W. Foley
-
Patent number: 4252942Abstract: A process for the preparation of benzothiazole-sulfenamides in which a benzothiazyl disulfide is reacted with a mixture comprising an amine halogenhydrate and an N-halogen amine derivative.Type: GrantFiled: October 5, 1979Date of Patent: February 24, 1981Assignee: Produits Chimiques Ugine KuhlmannInventors: Michel Alicot, Laurent Ciccotto, Adrien Tignol
-
Patent number: 4242513Abstract: Chromogenic compounds of normally colorless form are disclosed having the following structural formula: ##STR1## wherein E represents a six-membered aromatic or heterocyclic ring which may have an aromatic condensed ring and both the E ring and the condensed ring may be substituted, A represents an optionally substituted aminophenyl, indolyl, benzoindolyl, julolidinyl or kairolyl radical or the radical represented by B, and B represents a family of heterocyclic radicals. The compounds of this invention are eligible for use in pressure-sensitive and heat sensitive record materials and manifold marking systems.Type: GrantFiled: March 5, 1979Date of Patent: December 30, 1980Assignee: Appleton Papers Inc.Inventors: Troy E. Hoover, Sheldon Farber, William J. Becker
-
Patent number: 4231929Abstract: This invention relates to phenol sulfam(na)phthaleins possessing a 2-(2'-halomethylbenzoyl) group substituted on the N atom of the sulfam(na)phthalein ring, which compounds find utility as photographic optical filter agents and filter agent precursors.Type: GrantFiled: September 23, 1977Date of Patent: November 4, 1980Assignee: Polaroid CorporationInventors: Stanley M. Bloom, Alan L. Borror, James W. Foley
-
Patent number: 4227915Abstract: The present invention relates to compounds of the formula ##STR1## wherein X, Y and W represent independently oxygen or sulfur;T represents lower alkyl, lower alkoxy, halo, CF.sub.3 or NO.sub.2 ;m is an integer of from 0 to 2;n is an integer of from 1 to 3; andR is selected from the group consisting of ##STR2## morpholino, pyrrolidyl, pyrrolidyl substituted by from 1 to 2 lower alkyl or lower alkoxy moieties and ##STR3## where a is an integer of from 5 to 8 inclusive; R.sub.1 represents lower alkyl, lower alkenyl, benzyl, phenyl or phenyl substituted by from 1 to 3 lower alkyl, lower alkoxy, lower alkenyl, CF.sub.3 or NO.sub.2 moieties;R.sub.2 represents hydrogen, lower alkyl or lower alkenyl moieties, with the proviso that when X is oxygen, R.sub.1 and R.sub.2 cannot equal methyl. The invention also relates to the use of said compounds in a method of regulating leguminous plant growth as well as to plant growth regulant compositions.Type: GrantFiled: May 18, 1978Date of Patent: October 14, 1980Assignee: Monsanto CompanyInventor: John J. D'Amico
-
Patent number: 4228075Abstract: This invention relates to phenol sulfam(na)phthaleins possessing a ##STR1## group wherein R is selected from lower alkyl and phenyl, unsubstituted or substituted with at least one electron-withdrawing group on the N atom of the sulfam(na)phthalein ring, which compounds find utility as photographic optical filter agents and filter agent precursors.Type: GrantFiled: September 23, 1977Date of Patent: October 14, 1980Assignee: Polaroid CorporationInventors: Stanley M. Bloom, Alan L. Borror, James W. Foley
-
Patent number: 4210752Abstract: The present invention is concerned with synthesizing certain ##STR1## by reacting (a) a 3,3-disubstituted sulfam(na)phthalein wherein one of the 3-substituents is a 4'-hydroxy-1'-phenyl moiety or a 4'-hydroxy-1'-naphthyl moiety substituted in the 3'-position with a perhalomethylcarbinol group and (b) an acid halide, ##STR2## wherein W is chloro or bromo and Y is hydrogen or an electron-withdrawing group, preferably, in the presence of a zeolite molecular sieve or acid alumina to give (c) the corresponding ##STR3## The compounds produced are useful, for example, as pH-sensitive indicator dyes or as photographic light-screening dyes.Type: GrantFiled: November 2, 1978Date of Patent: July 1, 1980Assignee: Polaroid CorporationInventors: Louis Cincotta, James W. Foley
-
Patent number: 4208518Abstract: Compounds which have the general formula ##STR1## and those which can be obtained from them with a Vilsmeier type reagent and have the formula ##STR2## as well as salts thereof, are useful as anti-inflammatory agents.Type: GrantFiled: December 27, 1978Date of Patent: June 17, 1980Assignee: E. R. Squibb & Sons, Inc.Inventors: Peter C. Wade, Thomas P. Kissick
-
Patent number: 4204061Abstract: This invention relates to phenol sulfam(na)phthaleins possessing a ##STR1## wherein R is selected from methyl, unsubstituted or substituted with one or two halo groups and phenyl, unsubstituted or substituted with alkyl, dimethylamino or nitro substituted on the N atom of the sulfam(na)phthalein ring, which compounds find utility as photographic optical filter agents and filter agent precursors.Type: GrantFiled: September 23, 1977Date of Patent: May 20, 1980Assignee: Polaroid CorporationInventors: Stanley M. Bloom, Alan L. Borror, James W. Foley
-
Patent number: 4195180Abstract: This invention relates to 1-naphthol sulfam(na)phthaleins possessing a carbonyl moiety on the N atom of sulfam(na)phthalein ring, which compounds find utility, for example, as antihalation and filter dyes in photographic products and processes.Type: GrantFiled: September 23, 1977Date of Patent: March 25, 1980Assignee: Polaroid CorporationInventors: Alan L. Borror, Louis Cincotta, Ernest W. Ellis, James W. Foley
-
Patent number: 4191689Abstract: This invention relates to certain 3,3-di(4'-OP-carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxides (and-2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxides) and to the preparation thereof by reacting (a) at least 2 equivalents of (i) a 4'-OP-carbocyclic aryllithium compound wherein P is a protecting group compatible with organometallic reagents or (ii) a 4'-OP-carbocyclic arylMgE compound wherein P is a protecting group compatible with organometallic reagents and E is chloro, bromo or iodo and (b) 1 equivalent of a compound selected from a 3-chlorobenz[d] isothiazole-1,1-dioxide and a 3-chloronaphtho[1,8-de]-1,2-thiazine-1,1-dioxide to give the corresponding 3,3-di(4'-OP-carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxide or the corresponding 3,3-di(4'-OP-carbocyclic aryl)-2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxide, which compounds are useful in the synthesis of phenol and 1-naphthol sulfam(na)-phthaleins employed, for example, as photographic optical filter agents and filter agentType: GrantFiled: September 23, 1977Date of Patent: March 4, 1980Assignee: Polaroid CorporationInventors: Stanley M. Bloom, Alan L. Borror, James W. Foley
-
Patent number: 4182873Abstract: Thiazolesulphenamides, useful as rubber vulcanization accelerators, are made by reaction of a 2-mercapto-thiazole or a 2,2'-dithiazolyl disulphide with ammonia or a primary or secondary amine in the presence of oxygen and a copper catalyst of specified kind.Type: GrantFiled: June 2, 1975Date of Patent: January 8, 1980Assignee: Rhone-Poulenc S.A.Inventor: Raymond Janin
-
Patent number: 4178447Abstract: This invention relates to a method of synthesizing certain 3-(carbocyclic aryl)-3-(4'-OP-carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxides (and -2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxides) by reacting (a) a 4-OP-carbocyclic aryllithium compound wherein P is a protecting group and (b) a 3-(carbocyclic aryl)benz[d]isothiazole-1,1-dioxide wherein said 3-(carbocyclic aryl) moiety is other than a 3-(4'-OP-carbocyclic aryl) moiety to give (c) the corresponding 3-carbocyclic aryl)-3-(4'-OP-carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxide. The -2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxides are prepared in the same manner by reacting a 3-(carbocyclic aryl)naphtho[1,8-de]-1,2-thiazine-1,1-dioxide with said 4'-OP-carbocyclic aryllithium compound.Type: GrantFiled: September 23, 1977Date of Patent: December 11, 1979Assignee: Polaroid CorporationInventors: Alan L. Borror, James W. Foley, Marcis M. Kampe, John W. Lee, Jr.
-
Patent number: 4178446Abstract: This invention relates to phenol sulfam(na)phthaleins possessing a ##STR1## group wherein Y represents an electron-withdrawing group substituted on the N atom of the sulfam(na)phthalein ring, which compounds find utility as photographic optical filter agents and filter agent precursors.Type: GrantFiled: September 23, 1977Date of Patent: December 11, 1979Assignee: Polaroid CorporationInventors: Stanley M. Bloom, Alan L. Borror, James W. Foley