Benzothiazoles (including Hydrogenated) Patents (Class 544/135)
  • Patent number: 4696939
    Abstract: Compounds of the formula ##STR1## and their pharmaceutically acceptable salts, wherein the substituents are as defined herein, having antihypertensive activity.
    Type: Grant
    Filed: November 29, 1985
    Date of Patent: September 29, 1987
    Assignee: USV Pharmaceutical Corporation
    Inventors: John T. Suh, John J. Piwinski, Howard Jones, Edward S. Neiss
  • Patent number: 4692445
    Abstract: 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: Grant
    Filed: November 12, 1986
    Date of Patent: September 8, 1987
    Assignee: Rorer Pharmaceutical Corporation
    Inventors: Donald E. Kuhla, Henry F. Campbell, William L. Studt
  • Patent number: 4670556
    Abstract: 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: Grant
    Filed: July 6, 1984
    Date of Patent: June 2, 1987
    Assignee: AKZO NV
    Inventors: Hans Zengel, Ludwig Eisenhuth, Manfred Bergfeld
  • Patent number: 4621142
    Abstract: 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: Grant
    Filed: July 30, 1985
    Date of Patent: November 4, 1986
    Assignee: American Home Products Corporation
    Inventors: Anthony C. Scotese, Arthur A. Santilli, Donald P. Strike
  • Patent number: 4589910
    Abstract: 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: Grant
    Filed: April 30, 1985
    Date of Patent: May 20, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Hagen, Hans Ziegler, Bruno Wuerzer
  • Patent number: 4590192
    Abstract: 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: Grant
    Filed: September 29, 1983
    Date of Patent: May 20, 1986
    Assignee: Beecham Group p.l.c.
    Inventors: Charles S. Fake, Gordon Burrell
  • Patent number: 4589991
    Abstract: 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: Grant
    Filed: July 1, 1985
    Date of Patent: May 20, 1986
    Assignee: Exxon Research & Engineering Co.
    Inventors: Jack Ryer, Chung Kun Shih, John E. Williams
  • Patent number: 4590189
    Abstract: 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: Grant
    Filed: March 24, 1983
    Date of Patent: May 20, 1986
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Kentaro Hiraga, Yoshiaki Saji
  • Patent number: 4558125
    Abstract: 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: Grant
    Filed: May 21, 1984
    Date of Patent: December 10, 1985
    Assignee: Santen Pharmaceutical Co., Ltd.
    Inventors: Jun-ichi Iwao, Tadashi Iso, Masayuki Oya
  • Patent number: 4552969
    Abstract: 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: Grant
    Filed: May 21, 1984
    Date of Patent: November 12, 1985
    Assignee: Santen Pharmaceutical Co., Ltd.
    Inventors: Jun-ichi Iwao, Tadashi Iso, Masayuki Oya
  • Patent number: 4532062
    Abstract: 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: Grant
    Filed: January 23, 1984
    Date of Patent: July 30, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Jack Ryer, Ricardo Bloch, Harold E. Deen
  • Patent number: 4528375
    Abstract: Histamine H.sub.2 -receptor antagonists of the formula ##STR1## wherein A, m, Z, n and R.sup.
    Type: Grant
    Filed: April 16, 1984
    Date of Patent: July 9, 1985
    Assignee: Bristol-Myers Company
    Inventors: Ronnie R. Crenshaw, Aldo A. Algieri
  • Patent number: 4528378
    Abstract: Histamine H.sub.2 -receptor antagonists of the formula ##STR1## wherein A, m, Z, n and R.sup.
    Type: Grant
    Filed: April 16, 1984
    Date of Patent: July 9, 1985
    Assignee: Bristol-Myers Company
    Inventors: Ronnie R. Crenshaw, Aldo A. Algieri
  • Patent number: 4505923
    Abstract: Novel ethers of hydroxy-2-benzothiazolesulfonamide are useful for the topical treatment of elevated intraocular pressure. Ophthalmic compositions include drops and inserts.
    Type: Grant
    Filed: October 31, 1983
    Date of Patent: March 19, 1985
    Assignee: Merck & Co., Inc.
    Inventors: Jacob M. Hoffman, Jr., Otto W. Woltersdorf, Jr.
  • Patent number: 4499103
    Abstract: 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: Grant
    Filed: March 17, 1983
    Date of Patent: February 12, 1985
    Assignee: Merck & Co., Inc.
    Inventor: S. Jane de Solms
  • Patent number: 4490527
    Abstract: 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: Grant
    Filed: February 22, 1983
    Date of Patent: December 25, 1984
    Assignee: American Home Products Corporation
    Inventors: Guy A. Schiehser, Donald P. Strike
  • Patent number: 4479949
    Abstract: 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: Grant
    Filed: April 14, 1983
    Date of Patent: October 30, 1984
    Assignee: Santen Pharmaceutical Co., Ltd.
    Inventors: Jun-ichi Iwao, Tadashi Iso, Masayuki Oya
  • Patent number: 4474965
    Abstract: 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: Grant
    Filed: September 1, 1982
    Date of Patent: October 2, 1984
    Assignee: Monsanto Company
    Inventor: John J. D'Amico
  • Patent number: 4472417
    Abstract: 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: Grant
    Filed: April 22, 1983
    Date of Patent: September 18, 1984
    Assignee: Merck & Co., Inc.
    Inventor: Otto W. Woltersdorf, Jr.
  • Patent number: 4472418
    Abstract: 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: Grant
    Filed: April 22, 1983
    Date of Patent: September 18, 1984
    Assignee: Merck & Co., Inc.
    Inventor: Otto W. Woltersdorf, Jr.
  • Patent number: 4470991
    Abstract: 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: Grant
    Filed: April 22, 1983
    Date of Patent: September 11, 1984
    Assignee: Merck & Co., Inc.
    Inventor: Otto W. Woltersdorf, Jr.
  • Patent number: 4461897
    Abstract: 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: Grant
    Filed: September 24, 1982
    Date of Patent: July 24, 1984
    Assignee: Monsanto Europe S.A.
    Inventors: Alec S. Cobb, David J. Williams
  • Patent number: 4418030
    Abstract: 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: Grant
    Filed: December 15, 1981
    Date of Patent: November 29, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ernst-Willi Muller, Claus Rathjen
  • Patent number: 4409216
    Abstract: 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: Grant
    Filed: April 11, 1980
    Date of Patent: October 11, 1983
    Assignee: Beecham Group Limited
    Inventor: Barrie C. C. Cantello
  • Patent number: 4383850
    Abstract: 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: Grant
    Filed: April 13, 1982
    Date of Patent: May 17, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Reinhard Handte, Klaus Bauer, Hermann Bieringer
  • Patent number: 4371734
    Abstract: 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: Grant
    Filed: May 1, 1980
    Date of Patent: February 1, 1983
    Assignee: BASF Aktiengesellschaft
    Inventor: Guenther Seybold
  • Patent number: 4359574
    Abstract: 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: Grant
    Filed: August 4, 1980
    Date of Patent: November 16, 1982
    Assignee: Polaroid Corporation
    Inventors: Stanley M. Bloom, Alan L. Borror, James W. Foley
  • Patent number: 4344946
    Abstract: 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: Grant
    Filed: August 28, 1980
    Date of Patent: August 17, 1982
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Ernest Cullen, Genus Possanza, Patrick B. Stewart
  • Patent number: 4323677
    Abstract: N-amides of 2-benzothiazolinone have been found to be effective in regulating the growth of leguminous plants.
    Type: Grant
    Filed: June 25, 1979
    Date of Patent: April 6, 1982
    Assignee: Monsanto Company
    Inventor: John J. D'Amico
  • Patent number: 4311839
    Abstract: 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: Grant
    Filed: December 22, 1980
    Date of Patent: January 19, 1982
    Assignee: Polaroid Corporation
    Inventors: Alan L. Borror, Louis Cincotta, James W. Foley, Marcis M. Kampe
  • Patent number: 4299959
    Abstract: 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: Grant
    Filed: January 31, 1979
    Date of Patent: November 10, 1981
    Assignee: Ciba-Geigy Corporation
    Inventor: Nalin B. Desai
  • Patent number: 4293462
    Abstract: 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: Grant
    Filed: December 10, 1979
    Date of Patent: October 6, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert B. Woodward, Hans Bickel
  • Patent number: 4283538
    Abstract: 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: Grant
    Filed: December 26, 1979
    Date of Patent: August 11, 1981
    Assignee: Polaroid Corporation
    Inventor: James W. Foley
  • Patent number: 4283537
    Abstract: 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: Grant
    Filed: November 2, 1978
    Date of Patent: August 11, 1981
    Assignee: Polaroid Corporation
    Inventors: Louis Cincotta, James W. Foley
  • Patent number: 4259493
    Abstract: 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: Grant
    Filed: November 2, 1978
    Date of Patent: March 31, 1981
    Assignee: Polaroid Corporation
    Inventor: James W. Foley
  • Patent number: 4256744
    Abstract: 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: Grant
    Filed: February 2, 1979
    Date of Patent: March 17, 1981
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Shigeo Seki, Yashuharu Sekizawa, Fumio Kai, Yukio Suzuki, Michiaki Iwata, Tetsuro Watanabe
  • Patent number: 4255578
    Abstract: 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: Grant
    Filed: November 2, 1978
    Date of Patent: March 10, 1981
    Assignee: Polaroid Corporation
    Inventors: Louis Cincotta, James W. Foley
  • Patent number: 4252942
    Abstract: 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: Grant
    Filed: October 5, 1979
    Date of Patent: February 24, 1981
    Assignee: Produits Chimiques Ugine Kuhlmann
    Inventors: Michel Alicot, Laurent Ciccotto, Adrien Tignol
  • Patent number: 4242513
    Abstract: 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: Grant
    Filed: March 5, 1979
    Date of Patent: December 30, 1980
    Assignee: Appleton Papers Inc.
    Inventors: Troy E. Hoover, Sheldon Farber, William J. Becker
  • Patent number: 4231929
    Abstract: 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: Grant
    Filed: September 23, 1977
    Date of Patent: November 4, 1980
    Assignee: Polaroid Corporation
    Inventors: Stanley M. Bloom, Alan L. Borror, James W. Foley
  • Patent number: 4228075
    Abstract: 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: Grant
    Filed: September 23, 1977
    Date of Patent: October 14, 1980
    Assignee: Polaroid Corporation
    Inventors: Stanley M. Bloom, Alan L. Borror, James W. Foley
  • Patent number: 4227915
    Abstract: 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: Grant
    Filed: May 18, 1978
    Date of Patent: October 14, 1980
    Assignee: Monsanto Company
    Inventor: John J. D'Amico
  • Patent number: 4210752
    Abstract: 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: Grant
    Filed: November 2, 1978
    Date of Patent: July 1, 1980
    Assignee: Polaroid Corporation
    Inventors: Louis Cincotta, James W. Foley
  • Patent number: 4208518
    Abstract: 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: Grant
    Filed: December 27, 1978
    Date of Patent: June 17, 1980
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Peter C. Wade, Thomas P. Kissick
  • Patent number: 4204061
    Abstract: 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: Grant
    Filed: September 23, 1977
    Date of Patent: May 20, 1980
    Assignee: Polaroid Corporation
    Inventors: Stanley M. Bloom, Alan L. Borror, James W. Foley
  • Patent number: 4195180
    Abstract: 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: Grant
    Filed: September 23, 1977
    Date of Patent: March 25, 1980
    Assignee: Polaroid Corporation
    Inventors: Alan L. Borror, Louis Cincotta, Ernest W. Ellis, James W. Foley
  • Patent number: 4191689
    Abstract: 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 agent
    Type: Grant
    Filed: September 23, 1977
    Date of Patent: March 4, 1980
    Assignee: Polaroid Corporation
    Inventors: Stanley M. Bloom, Alan L. Borror, James W. Foley
  • Patent number: 4182873
    Abstract: 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: Grant
    Filed: June 2, 1975
    Date of Patent: January 8, 1980
    Assignee: Rhone-Poulenc S.A.
    Inventor: Raymond Janin
  • Patent number: 4178446
    Abstract: 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: Grant
    Filed: September 23, 1977
    Date of Patent: December 11, 1979
    Assignee: Polaroid Corporation
    Inventors: Stanley M. Bloom, Alan L. Borror, James W. Foley
  • Patent number: 4178447
    Abstract: 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: Grant
    Filed: September 23, 1977
    Date of Patent: December 11, 1979
    Assignee: Polaroid Corporation
    Inventors: Alan L. Borror, James W. Foley, Marcis M. Kampe, John W. Lee, Jr.