Sulfur Containing Hetero Ring (e.g., Thioxane, Etc.) Patents (Class 544/145)
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Patent number: 5041440Abstract: Novel dithiolane derivatives of formula: ##STR1## wherein X is, a C.sub.2 -C.sub.7 alkylcarbonyl group, benzoyl group, benzoyl group substituted with 1-3 groups selected from halogen, C.sub.1 -C.sub.4 alkyl, and C.sub.1 -C.sub.4 alkoxy; Y represents C.sub.2 -C.sub.7 alkylcarbonyl group, C.sub.2 -C.sub.7 alkoxycarbonyl group or cyano group; and R represents di (C.sub.1 -C.sub.4 alkylamino) group, morpholino group or piperidino group, are produced by reacting glyoxal sodium bisulfite adduct with amine compounds in the presence of acids and then with dithiolates. The dithiolane derivatives can activate liver functions and are effective for treatment and prophylaxis of hepatitis and other hepatic disorders.Type: GrantFiled: August 22, 1989Date of Patent: August 20, 1991Assignee: Nihon Nohyaku Co., Ltd.Inventors: Shuhei Kubota, Kunikazu Hiraga, Keisuke Nakayama, Matazaemon Uchida
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Patent number: 5037825Abstract: The invention relates to compounds of the formula ##STR1## wherein R.sup.1 is hydrogen, acyl, lower-alkyl or --CHO, --CH.sub.2 OR.sup.10, --COR.sup.7 or OR.sup.13 ; R.sup.2, R.sup.3 and R.sup.4 are, independently, hydrogen, lower-alkyl, lower-alkoxy or halogen; R.sup.5 and R.sup.6 are, independently, hydrogen or lower-alkyl; R.sup.7 is hydroxy, lower-alkoxy or NR.sup.8 R.sup.9 ; R.sup.8 and R.sup.9 are, independently, hydrogen or lower-alkyl; X and Y are, independently, >CR.sup.14 R.sup.15, --O--, --S--, >SO, >SO.sub.2 or >NR.sup.18 ; R.sup.10 and R.sup.18 are, independently, hydrogen, lower-alkyl or acyl; M is --C(R.sup.11).dbd.C(R.sup.12)--, --CONH-- or --NH--CO--; R.sup.11, R.sup.12, R.sup.14 and R.sup.15 are, independently, hydrogen or lower-alkyl, R.sup.Type: GrantFiled: July 10, 1989Date of Patent: August 6, 1991Assignee: Hoffmann-La Roche Inc.Inventors: Michael Klaus, Peter Mohr, Ekkehard Weiss
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Patent number: 5015656Abstract: A pharmaceutical compound of the formula ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 independently are hydrogen, hydroxy, halo, nitro, amino, C.sub.2-5 acylamino, C.sub.1-4 alkyl, --CHO, --CH.sub.2 OH, --CH.sub.2 OC.sub.1-4 alkyl, --COOH, --COC.sub.1-3 alkyl, --CH(OH)C.sub.1-3 alkyl, C.sub.1-4 alkoxy, C.sub.2-4 alkenyloxy, C.sub.1-4 alkylthio, C.sub.1-4 alkylsulphinyl, C.sub.1-4 alkylsulphonyl, N-substituted heterocyclyl, optionally substituted phenyl, optionally substituted phenylthio, optionally substituted phenylsulphinyl, optionally substituted phenylsulphonyl or optionally substituted phenylsulphonamido, or R.sup.1 and R.sup.2 together form a C.sub.3-5 alkylene bridge; provided that at least one of R.sup.2 and R.sup.3 is C.sub.1-4 alkoxy or C.sub.2-4 alkenyloxy; and X is (i) --(CH.sub.2).sub.n N(R.sup.4).sub.2 where each R.sup.4 independently is C.sub.1-4 alkyl, C.sub.2-4 alkenyl or optionally substituted C.sub.6 H.sub.5 CH.sub.Type: GrantFiled: September 26, 1989Date of Patent: May 14, 1991Assignees: Lilly S.A., Lilly Industries LimitedInventors: Maria I. F. Fernandez, Terrence M. Hotten, David E. Tupper
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Patent number: 4988727Abstract: A compound selected from the group consisting of all enantiomeric and diastereoisomeric forms possible of compounds of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, halogen, and alkyl and alkoxy of 1 to 5 carbon atoms, R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms, one of A and B being ##STR2## and the other being ##STR3## R is hydrogen or alkyl of 1 to 5 carbon atoms, Z is --(CH.sub.2).sub.n -- or branched alkylene of 2 to 8 carbon atoms, n is an integer from 0 to 5, Y is selected from the group consisting of naphthyl, indenyl, heterobicyclics and heteromonocyclic containing 5 to 6 ring members, all optionally substituted with at least one member of the group consisting of alkyl and alkoxy of 1 to 5 carbon atoms, halogen, --OH, --CF.sub.3, --NO.sub.2, --NH.sub.Type: GrantFiled: September 19, 1989Date of Patent: January 29, 1991Assignee: Roussel UclafInventors: Francois Clemence, Michel Fortin
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Patent number: 4968706Abstract: Compounds of formula I ##STR1## wherein Ar is an optionally substituted phenyl ring; B is a single bond, a group --(CH.sub.2 OCH.sub.2).sub.n being n=1 or 2, a 2,4-disubstituted-1,3-dioxolane ring or a 2,4-disubstituted-1,3-thioxolane ring, R is a single bond, an optionally substituted methylene or ethylene group and T is 2-, 3- or 4-pyridyl, an optionally salified or esterified carboxy group or a carboxyamide group. Said compounds are useful in treatment of respiratory diseases.Type: GrantFiled: August 11, 1988Date of Patent: November 6, 1990Assignee: Boehringer Mannhein Italia, S.p.A.Inventors: Silvano Spinelli, Roberto Di Domenico, Ernesto Menta, Bruno Lumachi, Licia Gallico, Sergio Tognella
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Patent number: 4962104Abstract: Fungicidal substituted 2-phenyl-2,2-difluoroethylthiolcarbonates of the formula ##STR1## in which R.sup.1 represents hydrogen, alkoxycarbonyl, alkoxyalkoxycarbonyl, alkylthioalkoxycarbonyl, halogenoalkoxycarbonyl, cyanoalkoxycarbonyl, alkenoxycarbonyl, alkynoxycarbonyl and cycloalkyloxycarbonyl, or represents cycloalkylalkoxycarbonyl,R.sup.2 represents hydrogen or alkyl, or represents phenyl, orR.sup.1 and R.sup.2 together represent the butadiene-1,4-diyl radical,R.sup.3 represents alkoxy, alkoxyalkoxy, alkylthioalkoxy, fluoroalkoxy, cyanoalkoxy, alkenoxy, alkynoxy, cycloalkyloxy and cycloalkylalkoxy, or represents the group ##STR2## in which R.sup.4 represents alkyl, alkoxyalkyl, alkylthioalkyl, cyanoalkyl, fluoroalkyl, alkenyl, alkinyl or cycloalkyl,R.sup.5 represents hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl, fluoroalkyl, cyanoalkyl, alkenyl, alkinyl or cycloalkyl, orR.sup.4 and R.sup.Type: GrantFiled: December 6, 1989Date of Patent: October 9, 1990Assignee: Bayer AktiengesellschaftInventors: Werner Daum, Dietmar Bielefeldt, Wilhelm Brandes
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Patent number: 4877779Abstract: Novel compounds and their salts are disclosed having the Formulas: ##STR1## wherein: R.sub.1 is hydrogen, phenyl, 9H-fluoren-9-yl, 10,11-dihydro-5H-dibenzo [a,d]cyclohepten-5-yl, 5H-dibenzo[a,d]cyclohepten-5-yl, 1,2,3,4-tetrahydro-1-naphthyl, 9H-xanthen-9-yl, 9H-thioxanthen-9-yl, 2-chloro-9H-thioxanthen-9-yl, 4H-chromanyl, diphenylmethyl, phenylcycloalkylmethyl wherein the bridgehead methylene may optionally be substituted with a hydroxy group and any of the phenyl or benzo-fused rings may be substituted with one or more R.sub.5 groups wherein R.sub.5 is selected from halogen, trifluoromethyl, lower alkyl, hydroxy or lower alkoxy groups; andR.sub.2 and R.sub.3, which may be the same or different, are hydrogen, lower alkyl, phenylalkyl (C.sub.1 -C.sub.5), wherein the phenyl ring may be substituted with one or more R.sub.5 groups or NR.sub.2 R.sub.Type: GrantFiled: May 17, 1988Date of Patent: October 31, 1989Assignee: Marion Laboratories, Inc.Inventors: Waclaw J. Rzeszotarski, Maria E. Guzewska, John P. Carter, Theodore C. Adams, Andrea C. Dupont, Carl Kaiser
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Patent number: 4876271Abstract: Novel substituted thieno[3,2-b]thiophene-2-sulfonamides are prepared by novel synthetic processes. These compounds are useful for the treatment of elevated intraocular pressure in compositions including ophthalmic drops and inserts.Type: GrantFiled: December 20, 1988Date of Patent: October 24, 1989Assignee: Merck & Co., Inc.Inventors: George D. Hartman, John D. Prugh
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Patent number: 4824968Abstract: Aromatic sulfonamides with a saturated heterocycle fused thereto are carbonic anhydrase inhibitors useful in the treatment of elevated intraocular pressure.Type: GrantFiled: June 26, 1987Date of Patent: April 25, 1989Assignee: Merck & Co., Inc.Inventors: Gerald S. Ponticello, J. Mark Wiggins
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Patent number: 4816475Abstract: An anti-arteriosclerotic or anti-hyperlipemic 1,3,5-trithiane derivative according to the formula (I): ##STR1## a pharmaceutical composition containing the same, and a process for producing the same.Type: GrantFiled: July 14, 1987Date of Patent: March 28, 1989Assignee: Nihon Nohyaku Co. Ltd.Inventors: Masashi Nagamine, Kunikazu Hiraga, Atsushi Sakai, Matazaemon Uchida
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Patent number: 4797413Abstract: Aromatic sulfonamides with a saturated heterocycle fused thereto are carbonic anhydrase inhibitors useful in the treatment of elevated intraocular pressure.Type: GrantFiled: June 26, 1987Date of Patent: January 10, 1989Assignee: Merck & Co., Inc.Inventors: John J. Baldwin, Gerald S. Ponticello, Marcia E. Christy
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Patent number: 4788192Abstract: Novel 2-sulfamoylbenzo[b]thiopenes and derivatives thereof are shown to be useful for the treatment of elevated intraocular pressure in compositions including ophthalmic drops and inserts.Type: GrantFiled: March 12, 1987Date of Patent: November 29, 1988Assignee: Merck & Co., Inc.Inventors: Kenneth L. Shepard, Samuel L. Graham
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Patent number: 4775672Abstract: Novel aminoalkylthiodibenzothiepins and related compounds, physiologically tolerable acid addition salts thereof, a method of preparing same, pharmaceutical and veterinary preparations including same and methods of treating by administering same are disclosed. These compounds are useful as antidepressant, analgetic, and anticonvulsant agents.Type: GrantFiled: February 13, 1987Date of Patent: October 4, 1988Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Helen H. Ong, Vernon B. Anderson, James A. Profitt
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Patent number: 4771069Abstract: Novel aminoalkylthiodibenzothiepins and related compounds, physiologically tolerable acid addition salts thereof, a method of preparing same, pharmaceutical and veterinary preparations including same and methods of treating by administering same are disclosed. These compounds are useful as antidepressant, analgetic, and anticonvulsant agents.Type: GrantFiled: February 11, 1987Date of Patent: September 13, 1988Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Helen H. Ong, Vernon B. Anderson, James A. Profitt
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Patent number: 4757151Abstract: Certain 2-substituted-[2-substituted-amino]-N-arylalkyl-3-[indol-3-yl]propanamides demonstrate activity as appetite suppressants. The compounds, pharmaceutical compositions, and a method of suppressing appetite are disclosed.Type: GrantFiled: September 30, 1986Date of Patent: July 12, 1988Assignee: Warner-Lambert CompanyInventor: David C. Horwell
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Patent number: 4751316Abstract: Novel 1,5-benzoxathiepin derivatives of the formula: ##STR1## [wherein R.sub.1 and R.sub.2 are independently hydrogen, halogen, hydroxy, lower alkyl or lower alkoxy; R.sub.3 and R.sub.4 are independently hydrogen, optionally substituted lower alkyl or optionally substituted cycloalkyl or optionally substituted aralkyl, or both jointly form an optionally substituted ring together with the adjacent nitrogen atom; X is hydrogen, optionally substituted lower alkyl, optionally substituted aryl or a carboxyl group which may be esterified or amidated; Y is >C.dbd.O or >CH--OR.sub.5 (wherein R.sub.5 is hydrogen, acyl or optionally substituted carbamoyl); m is an integer of 0 to 2; n is an integer of 1 to 6] and salts thereof exhibit serotonin S.sub.Type: GrantFiled: April 15, 1987Date of Patent: June 14, 1988Assignee: Takeda Chemical Industries, Ltd.Inventors: Hirosada Sugihara, Minoru Hirata
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Patent number: 4737514Abstract: Compounds of formula (I) ##STR1## wherein n is 0, 1 or 2;one or R.sup.1 and R.sup.2 is hydrogen and the other is selected from carbamoyl, N-C.sub.1-4 alkylcarbamoyl, N,N-di-C.sub.1-4 alkylcarbamoyl, carbamimidoyl, N.sup.1 -C.sub.1-4 alkylcarbamimidoyl, N.sup.2 -C.sub.1-4 alkylcarbamimidoyl, N.sup.1 -C.sub.1-4 alkyl-N.sup.2 -C.sub.1-4 alkylcarbamimidoyl, N.sup.1,N.sup.1 -di-C.sub.1-4 alkylcarbamimidoyl, N.sup.1,N.sup.1 -di-C.sub.1-4 alkyl-N.sup.2 -C.sub.1-4 alkylcarbamimidoyl and imidazolin-2-yl (optionally substituted by one or more C.sub.1-4 alkyl groups); andR.sup.3 is selected from hydrogen, saturated and unsaturated aliphatic hydocarbon moieties containing from 1 to 4 carbon atoms, groups OR.sup.4 (where R.sup.4 is selected from hydrogen and saturated and unsaturated aliphatic hydrocarbon moieties containing from 1 to 4 carbon atoms), halo, groups of formula--NR.sup.5 R.sup.6 (where R.sup.5 and R.sup.6 are independently selected from hydrogen, C.sub.1-4 alkyl and hydroxy C.sub.Type: GrantFiled: January 2, 1986Date of Patent: April 12, 1988Assignee: Burroughs Wellcome Co.Inventors: Morton Harfenist, Charles T. Joyner, Darryl J. Heuser
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Patent number: 4737494Abstract: A 1,3-dithiole derivative having the formula: ##STR1## wherein each of R.sup.1 and R.sup.2 is a substituted or unsubstituted alkyl, cycloalkyl, lower alkenyl, lower alkynyl, aryl or aralkyl group or R.sup.1 and R.sup.2 together form a substituted or unsubstituted alkylene or alkenylene group having from 3 to 6 carbon atoms, which may contain a cycloalkylene group, an o-phenylene group or a hetero atom selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom which may have a substituent, and Q is an acid residue useful for the treatment of liver diseases.Type: GrantFiled: December 26, 1985Date of Patent: April 12, 1988Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Mitsuo Yano, Yoshimi Tsuchiya, Yukio Hirayama, Kyoko Nakamichi, Junji Yoshizawa
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Patent number: 4677103Abstract: Novel labdanes, intermediates and processes for the preparation thereof, and methods for reducing intraocular pressure utilizing compounds or compositions thereof are disclosed.Type: GrantFiled: October 20, 1986Date of Patent: June 30, 1987Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Raymond W. Kosley, Jr., Robert J. Cherill
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Patent number: 4672064Abstract: Novel 1,5-benzoxathiepin derivatives of the formula: ##STR1## [wherein R.sub.1 and R.sub.2 are independently hydrogen, halogen, hydroxy, lower alkyl or lower alkoxy; R.sub.3 and R.sub.4 are independently hydrogen, optionally substituted lower alkyl or optionally substituted cycloalkyl or optionally substituted aralkyl, or both jointly form an optionally substituted ring together with the adjacent nitrogen atom; X is hydrogen, optionally substituted lower alkyl, optionally substituted aryl or a carboxyl group which may be esterified or amidated; Y is ##STR2## (wherein R.sub.5 is hydrogen, acyl or optionally substituted carbamoyl); m is an integer of 0 to 2; n is an integer of 1 to 6] and salts thereof exhibit serotonin S.sub.Type: GrantFiled: December 10, 1985Date of Patent: June 9, 1987Assignee: Takeda Chemical Industries, Ltd.Inventors: Hirosada Sugihara, Minoru Hirata
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Patent number: 4668695Abstract: Novel aminoalkylthiodibenzothiepins and related compounds, physiologically tolerable acid addition salts thereof, a method of preparing same, pharmaceutical and veterinary preparations including same and methods of treating by administering same are disclosed. These compounds are useful as antidepressant, analgetic, and anticonvulsant agents.Type: GrantFiled: October 28, 1983Date of Patent: May 26, 1987Assignee: Hoechst Roussel Pharmaceuticals Inc.Inventors: Helen H. Ong, Vernon B. Anderson, James A. Profitt
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Patent number: 4666904Abstract: Novel aminoacyllabdanes, intermediates and processes for the preparation thereof, and methods for reducing intraocular pressure utilizing compounds or compositions thereof are disclosed.Type: GrantFiled: October 20, 1986Date of Patent: May 19, 1987Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Raymond W. Kosley, Jr., Robert J. Cherill
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Patent number: 4665202Abstract: The invention relates to pharmaceutical preparations containing compounds of formula I ##STR1## in which X.sub.1 and X.sub.2, independently of each other, represent hydrogen, halogen, unsubstituted or substituted amino or a quaternary ammonium salt; etherified or esterified hydroxy; free, etherified, esterified or oxidized mercapto; nitro; functionally modified formyl; free or functionally modified carboxyl; acyl; an unsubstituted or substituted hydrocarbon radical, or an unsubstituted or substituted heterocyclic radical; with the proviso that at least one of the radicals X.sub.1 and X.sub.2 is bonded by a carbon atom to the ring system and with the proviso that X.sub.1 and X.sub.2 cannot be together halogen and formyl; in which Y represents oxygen, sulfur, sulfinyl or sulfonyl but must be sulfur, sulfinyl or sulfonyl, if X.sub.1 is hydrogen and X.sub.Type: GrantFiled: August 24, 1984Date of Patent: May 12, 1987Assignee: Zyma SAInventors: Christian G. Rimbault, Philippe M. Narbel
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Patent number: 4645758Abstract: The invention concerns:Novel dibenz/b,e/oxepin and dibenz/b,e/thiepin compounds having the general formula: ##STR1## wherein X is O or S,R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and are each selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower alkynyl, lower cycloalkyl, lower alkoxy, lower alkylthio, lower alkylsulphinyl, lower alkylsulponyl, halogen, trifluoromethyl, trifluoromethylthio, lower dialkylsulphonamido, nitro, hydroxy, cyano, carbamyl, carboxy, lower alkoxycarbonyl, amino, N-lower alkylamino, N,N-diloweralkylamino, lower acylamido, lower alkanesulfonamido and lower acyl and, when on adjacent carbon atoms at the positions 2 and 3 and/or 8 and 9, two of the substituents R.sup.1 and R.sup.2 or R.sup.3 and R.sup.4 taken together may form a methylenedioxy group;R.sup.5 and R.sup.Type: GrantFiled: January 17, 1986Date of Patent: February 24, 1987Inventors: Nils-Erik Willman, Bengt C. H. Sjogren, Lennart G. Nordh, Gustav L. Persson, Goran H. Sjoholm
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Patent number: 4640929Abstract: A novel 1,3-dithiane of the formula ##STR1## wherein R.sup.1 is a di-substituted amino group; R.sup.2 and R.sup.3 are such that one of them is an electron-withdrawing group with the other being a hydrogen atom, a hydrocarbon group or heterocyclic group of the class consisting of thienyl, triazolyl, and pyridyl, which may optionally be substituted or that R.sup.2 and R.sup.3 taken together with the adjacent carbon atom form a spiro ring provided that at least one of R.sup.2 and R.sup.3 is a carbonyl group; X.sup.1 and X.sup.2 each is a sulfur atom and at least one of X.sup.1 and X.sup.2 may be oxidized, or a salt thereof, possesses very useful pesticidal actions.Type: GrantFiled: August 23, 1983Date of Patent: February 3, 1987Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroyuki Mitsudera, Kazuo Konishi, Yasuo Sato
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Patent number: 4624962Abstract: Compounds of the formula I ##STR1## in which n denotes 0-3,R.sup.1 and R.sup.1' are the same or different and denote hydrogen, alkyl or alkenyl, phenyl or benzyl, each substituted as desired;R.sup.2 denotes hydrogen, alkyl or alkenyl;R.sup.3 denotes hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl or aminoalkyl, alkanoylaminoalkyl, guanidinoalkyl, imidazolylalkyl, indolylalkyl, mercaptoalkyl or alkylthioalkyl, phenylalkyl, hydroxphenylalkyl, phenoxyalkyl or phenylthioalkyl, or R.sup.2 and R.sup.3, together with the C and N atoms carrying them, denote a saturated or unsaturated 4- to 8-membered monocyclic or 8- to 10-membered bicyclic isocycle or heterocycle, optionally monosubstituted or disubstituted by hydroxyl, alkoxy having 1 to 3 C atoms or alkyl,R.sup.4 denotes hydrogen, alkyl, alkenyl, alkadienyl, alkinyl, alkeninyl or alkadiinyl, cycloalkyl, phenyl, benzyl, phenethyl or phenylpropyl, each of which can be optionally monosubstituted or disubstituted;R.sup.5 denotes hydrogen or alkyl, hydroxyl or alkoxy andR.Type: GrantFiled: February 1, 1985Date of Patent: November 25, 1986Assignee: Hoechst AktiengesellschaftInventors: Rainer Henning, Hansjorg Urbach, Rolf Geiger, Volker Teetz, Bernward Scholkens
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Patent number: 4624949Abstract: The invention relates to compounds having the general formula (I) ##STR1## wherein R.sub.1 is carboxy, esterified carboxy or an amide of formula ##STR2## in which R.sub.9 is hydrogen or C.sub.1 -C.sub.6 alkyl, A is C.sub.2 -C.sub.6 alkylene and R.sub.a and R.sub.b are hydrogen or C.sub.1 -C.sub.6 alkyl or R.sub.a and R.sub.b taken together with the nitrogen atom to which they are linked form a saturated, optionally substituted, heteromonocyclic ring;R.sub.2 is hydrogen or C.sub.1 -C.sub.6 alkyl;each of R.sub.3 to R.sub.8 is independently hydrogen, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.4 alkenyloxy or C.sub.1 -C.sub.6 alkoxy; and the pharmaceutically acceptable salts thereof, which are useful as immunomodulating and anti-viral agents.Type: GrantFiled: March 4, 1986Date of Patent: November 25, 1986Assignee: Farmitalia Carlo Erba, S.p.A.Inventors: Piero Melloni, Paolo Salvadori, Pier P. Lovisolo
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Patent number: 4623486Abstract: Certain novel p-aminomethylbenzoyl derivatives of 4-hydroxy-2-methyl-N-(2-pyridinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide and several other closely-related known oxicams have been prepared. These particular compounds are useful in therapy as prodrug forms of the known anti-inflammatory and analgesic oxicams. Preferred member compounds include 2-methyl-4-[4-(morpholinomethyl)benzoyloxy]-N-(2-pyridinyl)-2H-1,2-benzoth iazine-3-carboxamide 1,1-dioxide, 2-methyl-4-[4-(piperidinomethyl)benzoyloxy]-N-(2-pyridinyl)-2H-1,2-benzoth iazine-3-carboxamide 1,1-dioxide, 2-methyl-N-(6-methyl-2-pyridinyl)-4-[4-(piperidinomethyl)benzoyloxy]-2H-1, 2-benzothiazine-3-carboxamide 1,1-dioxide, 2-methyl-4-[4-(4-methylpiperazinomethyl)benzoyloxy]-N-(2-pyridinyl)-2H-1,2 -benzothiazine-3-carboxamide 1,1-dioxide and 2-methyl-4-[4-(pyridiniummethyl)benzoyloxy]-N-(2-pyridinyl)-2H-1,2-benzoth iazine-3-carboxamide 1,1-dioxide chloride. Methods for preparing these compounds from known starting materials are provided.Type: GrantFiled: May 29, 1985Date of Patent: November 18, 1986Assignee: Pfizer Inc.Inventor: Joseph G. Lombardino
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Patent number: 4619944Abstract: Provided are antihypertensive compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are hydrogen, alkyl, alkenyl, alkynyl, phenyl-alkyl, or cycloalkyl, and may be the same or different,m is an integer from 0 to 2 inclusive,n is an integer from 0 to 4 inclusive,M is alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycycloalkyl-alkyl, aryl, aralkyl, heteroaryl, heteroaryl-alkyl, hetero-cycloalkyl, hetero-cycloalkyl-alkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused heteroaryl-cycloalkyl, fused heteroaryl-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, or dialkylaminoalkyl.Y is hydroxy, alkoxy, amino, or substituted amino, aminoalkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, andR.sub.7 is alkyl, aryl, aralkyl, cycloalkyl, cycloalkyl-alkyl, heterocyclic, --CO--SR, --CS--SR, ##STR2## CH.sub.2 CO.sub.2 R, --CHM--CO.sub.2 R, --CH.sub.2 --CO--SR, --CN, ##STR3## --CO--NH--CH.sub.2 CO.sub.2 R, ##STR4## or --CO--CO.sub.Type: GrantFiled: February 19, 1985Date of Patent: October 28, 1986Assignee: USV Pharmaceutical CorporationInventors: Raymond D. Youssefyeh, Howard Jones
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Patent number: 4614821Abstract: This invention relate to a process for producing a 1,2,3-trithiane compound of the general formula: ##STR1## wherein each of R.sub.1 and R.sub.2 is independently a lower alkyl group, or alternatively, R.sub.1 and R.sub.2 together with the adjacent nitrogen atom form a 5- or 6-membered heterocyclic group which may further contain an oxygen, sulfur or nitrogen atom, or a salt thereof, which comprises reacting a compound of the general formula: ##STR2## wherein R.sub.1 and R.sub.2 are as defined above, or a salt thereof with a compound of the general formula:Me.sub.2 S (II)wherein Me is hydrogen, an alkali metal atom or an ammonium radical under an acid condition.The compound (I) or a salt thereof is produced in high purity and high yield.Type: GrantFiled: January 16, 1986Date of Patent: September 30, 1986Assignee: Takeda Chemical Industries, Ltd.Inventors: Kazuaki Kihara, Makoto Kuroda
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Patent number: 4610983Abstract: This invention relates to a novel N-acyl acidic amino acid diamide derivative represented by the general formula or a salt thereof: ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, represents a hydrogen atom or a substituted or unsubstituted alkyl, cycloalkyl, alkenyl or aralkyl group, or R.sup.1 and R.sup.2 and/or R.sup.3 and R.sup.4, when taken together with the respective adjacent nitrogen atoms, form a substituted or unsubstituted heterocyclic group; R.sup.5 represents a substituted or unsubstituted cycloalkyl, acyl or heterocyclic group; A represents a bond or a substituted or unsubstituted alkylene, alkenylene or alkadienylene group; and n is 1, 2 or 3. Said compound has an anti-ulcer activity which is effective to human beings and animals. This disclosure relates to such a compound, to a process for the production thereof and to an anti-ulcer agent containing the same.Type: GrantFiled: December 3, 1984Date of Patent: September 9, 1986Assignee: Toyama Chemical Co., Ltd.Inventors: Noboru Takagawa, Shiro Hirai, Takuya Kodama, Hiroshi Hirano, Yasuo Kiba, Mikio Kawabata, Tatsuya Miyaura, Yasuyuki Suzuki
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Patent number: 4563291Abstract: A method of manufacture of a substituted amino-alkyl sulfonic acid zwitterion is presented. The compound is prepared by the reaction of an epoxide with bisulfite which then is reacted with a secondary amine to form the amino-alkyl sulfonic acid or a salt thereof. Selected compounds can be utilized as a buffer composition to form viscosified fluids for use in the treatment of subterranean formations. The remaining amino-alkyl sulfonic acids or salts can be used as surfactants.Type: GrantFiled: July 20, 1984Date of Patent: January 7, 1986Assignee: Halliburton CompanyInventor: Glenn S. Penny
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Patent number: 4551472Abstract: Unsymmetrical N-substituted bis-carbamoyl sulfide compounds exhibit exceptional broad spectrum pesticidal activity coupled with extremely low mammalian toxicity and phytotoxicity.Type: GrantFiled: January 9, 1984Date of Patent: November 5, 1985Assignee: Union Carbide CorporationInventor: Themistocles D. J. D'Silva
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Patent number: 4542130Abstract: MIcrobicidally active 5-aminomethyl-1,3-oxathiolanes of the formula ##STR1## in which R.sup.1 is tetrahydronaphthyl, decahydronaphthyl or optionally substituted naphthyl, optionally substituted cycloalkyl or cycloalkenyl, optionally substituted phenyl, or alkyl which is substituted by phenyl, phenoxy, phenylthio, cyclohexyl, cyclohexyloxy or cyclohexylthio, each of which is optionally substituted,R.sup.2 is hydrogen or methyl,R.sup.3 is alkyl, andR.sup.4 is alkyl, alkenyl or optionally substituted aralkyl, orR.sup.3 and R.sup.4, together with the nitrogen atom to which they are bonded, form an optionally substituted saturated heterocyclic structure which can contain further heteroatoms,or a plant-tolerated addition product thereof with an acid or metal salt.Type: GrantFiled: June 27, 1984Date of Patent: September 17, 1985Assignee: Bayer AktiengesellschaftInventors: Joachim Weissmuller, Wolfgang Kramer, Dieter Berg, Paul Reinecke, Wilhelm Brandes, Gerd Hanssler
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Patent number: 4539412Abstract: 7-Hydroxylucanthone and 7-hydroxyhycanthone derivatives have been found to have significant antitumor effect. The derivatives are of the general formula: ##STR1## wherein the radicals R.sup.1 and R.sup.2 are lower alkyl groups or other simple groups and R.sup.3 is OH where X.dbd.O, and H or OH where X.dbd.S.Type: GrantFiled: February 1, 1984Date of Patent: September 3, 1985Assignee: Rensselaer Polytechnic InstituteInventor: Sydney Archer
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Patent number: 4515803Abstract: Compounds of the formula I ##STR1## in which n denotes 0-3,R.sup.1 and R.sup.1' are the same or different and denote hydrogen, alkyl or alkenyl, phenyl or benzyl, each substituted as desired;R.sup.2 denotes hydrogen, alkyl or alkenyl;R.sup.3 denotes hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl or aminoalkyl, alkanoylaminoalkyl, guanidinoalkyl, imidazolylalkyl, indolylalkyl, mercaptoalkyl or alkylthioalkyl, phenylalkyl, hydroxyphenylalkyl, phenoxyalkyl or phenylthioalkyl, or R.sup.2 and R.sup.3, together with the C and N atoms carrying them, denote a saturated or unsaturated 4- to 8-membered monocyclic or 8- to 10-membered bicyclic isocycle or heterocycle, optionally monosubstituted or disubstituted by hydroxyl, alkoxy having 1 to 3 C atoms or alkyl,R.sup.4 denotes hydrogen, alkyl, alkenyl, alkadienyl, alkinyl, alkeninyl or alkadiinyl, cycloalkyl, phenyl, benzyl, phenethyl or phenylpropyl, each of which can be optionally monosubstituted or disubstituted;R.sup.5 denotes hydrogen or alkyl, hydroxyl or alkoxy andR.Type: GrantFiled: September 1, 1982Date of Patent: May 7, 1985Assignee: Hoechst AktiengesellschafatInventors: Rainer Henning, Hansjorg Urbach, Rolf Geiger, Volker Teetz, Bernward Scholkens
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Patent number: 4506083Abstract: Thioxanthonecarboxylic acid esters, thioesters or amides of the formula I ##STR1## in which X and Z are hydrogen or one of the substituents defined in more detail in claim 1 and Y is --OR.sub.1, --SR.sub.1 or --N(R.sub.1)(R.sub.2), in which R.sub.1 is C.sub.1-24 alkyl and R.sub.2 is H or R.sub.1, are suitable, if desired together with amines, as initiators for the photopolymerization of ethylenically unsaturated compounds or for photochemical crosslinking of polyolefines. They are also used an sensitizers for photocrosslinkable polymers. They can be prepared by methods known per se, for example by cyclization of phenylthio-phthalic, -isophthalic or -terephthalic acids, which can be correspondingly substituted, and subsequent reaction with suitable alcohols, thiols or amines.Type: GrantFiled: June 28, 1982Date of Patent: March 19, 1985Assignee: Ciba-Geigy CorporationInventors: Vratislav Kvita, Hans Zweifel, Martin Roth, Louis Felder
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Patent number: 4500715Abstract: 1,3,4-Thiazole derivatives of the formula ##STR1## wherein R.sub.26 ' denotes a C.sub.1 -C.sub.8 -alkyl radical which is optionally substituted by hydroxyl, halogen, cyano, C.sub.1 -C.sub.4 -alkoxy, carboxyl, aminocarbonyl or C.sub.1 -C.sub.4 -alkoxycarbonyl, a C.sub.2 -C.sub.4 -alkenyl radical, a cyclohexyl radical which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, a phenyl, benzyl or phenylethyl radical which is optionally substituted by halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, a C.sub.1 -C.sub.2 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, mono- or di-C.sub.1 -C.sub.4 -alkylaminocarbonyl, aminocarbonyl, mono- or di-C.sub.1 -C.sub.4 -alkylaminosulphonyl, 2-thienyl, 2-furyl, 2-tetrahydrofuryl, amino, C.sub.1 -C.sub.4 -alkylamino or di-(C.sub.1 -C.sub.4 -alkyl)-amino radical or a phenylamino or benzylamino radical which is optionally substituted by C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy and R.sub.27 ' denotes a C.sub.1 -C.sub.Type: GrantFiled: January 26, 1981Date of Patent: February 19, 1985Assignee: Bayer AktiengesellschaftInventor: Hauke Furstenwerth
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Patent number: 4463176Abstract: A process for resolving a racemic modification of .beta.-adrenergic aryl- or hetaryl-oxypropanolamines such as (.+-.)-2-[2-hydroxy-3-[[2-(1H-indol-3-yl)-1,1-dimethylethyl]amino]propoxy] benzonitrile into its individual enantiomers is described. The process comprises converting the racemic modification into a pair of diastereomeric urea derivatives by reaction with a chiral aralkylisocyanate; separation into the individual diastereomers; and facile regeneration of the starting amine by cleavage of the intermediate urea compound using hydrazine. This final step is improved by the addition of an .alpha.-keto carboxylic acid, such as pyruvic acid, which functions as a scavenger of nucleophilic by-products.Type: GrantFiled: September 13, 1982Date of Patent: July 31, 1984Assignee: Mead Johnson & CompanyInventors: Ronald D. Dennis, Terence M. Dolak, William E. Kreighbaum
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Patent number: 4424213Abstract: Novel heterobicyclic compounds of Formula I, processes for preparing same and pesticidal compositions and methods are described.Type: GrantFiled: November 2, 1981Date of Patent: January 3, 1984Assignee: SDS Biotech CorporationInventors: Thomas A. Magee, Robert D. Battershell, Lawrence E. Limpel, Andrew W. Ho, Arthur W. Friedman, H. Glenn Corkins, William W. Brand, Russell Buchman, Louis Storace, Edmond R. Osgood
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Patent number: 4407797Abstract: New compounds of the formula: ##STR1## wherein X.sup..crclbar. is an anion, R is (C.sub.1-7) alkyl [unsubstituted or substituted by hydroxy, carboxy, alkoxycarbonyl, cyano, dialkylamino, alkylcarbonyl, or benzoyl which is unsubstituted or substituted by one or more halogen atoms or radicals selected from alkyl (optionally substituted by one or more halogens), alkoxy, hydroxy, amino, alkylamino, dialkylamino, cyano and nitro, or by a thenoyl radical (which is unsubstituted or substituted by one or more halogens or radicals selected from alkyl, cyano and nitro), or a pyridinecarbonyl, carbamoyl or dialkylcarbamoyl radical (the alkyl radicals of which can form a 5-membered or 6-membered heterocyclic ring) or a pyridyl radical], dialkylcarbamoyl (the alkyl radicals of which can form a 5-membered or 6-membered heterocyclic ring), (C.sub.2-4) alkenyl, (C.sub.2-4) alkynyl, alkoxycarbonyl or a 2-oxotetrahydrofuran-3-yl or 2-oxotetrahydropyran-3-yl ring, and either R.sub.1 and R.sub.Type: GrantFiled: August 10, 1982Date of Patent: October 4, 1983Assignee: Rhone-Poulenc SanteInventors: Claude Cotrel, Daniel Farge, Gerard Taurand
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Patent number: 4385182Abstract: Novel thioxanthonecarboxylic acids and thioxanthonecarboxylic acid derivatives of the formula I ##STR1## in which Y is --COOH, --CO-halogen, --CN or a carboxylic acid ester, thioester or amide group and X, Z and W are as defined in the patent claim, are described. The compounds of the formula I in which Y is other than --CO--halogen are suitable as sensitizers for photo-crosslinkable polymers or as initiators for photo-polymerization of ethylenically unsaturated compounds or for photo-chemical crosslinking of polyolefins. The acid halides of the formula I are starting materials for the preparation of the corresponding nitriles and carboxylic acid esters, thioesters and amides.Type: GrantFiled: April 28, 1981Date of Patent: May 24, 1983Assignee: Ciba-Geigy CorporationInventors: Walter Fischer, Vratislav Kvita, Hans Zweifel, Louis Felder
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Patent number: 4374984Abstract: Compounds of the formula ##STR1## wherein the substituents A, Z, R.sup.1, R.sup.2, R.sup.3, R.sup.4, X, n and m are defined hereinbeloware effective photoinitiators, especially for the photopolymerization of ethylenically unsaturated compounds and for the curing of printing inks.Type: GrantFiled: March 4, 1981Date of Patent: February 22, 1983Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Jurgen Eichler, Claus Herz, Karl-Heinz Neisius, Gregor Wehner
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Patent number: 4368329Abstract: A method of preparing a compound of the general formula: ##STR1## in which: R.sup.1 and R.sup.2 independently represent a hydrogen atom, an alkyl or substituted alkyl group, an aryl or substituted aryl group, an aralkyl or substituted aralkyl group, a cycloaliphatic or substituted cycloaliphatic group or a heterocyclic or substituted heterocyclic group providing R.sup.1 and R.sup.2 do not both represent cyclic groups of aromatic nature, or R.sup.1 and R.sup.2 together may represent the necessary atoms to complete a non-aromatic heterocyclic ring,R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently represent a hydrogen atom or any substituent providing the sum of their .sigma..sub.p constants has a value of less than +0.5, or R.sup.3 and R.sup.4 and/or R.sup.5 and R.sup.6 may represent the necessary atoms to complete an alicyclic or aromatic ring, R.sup.3 and R.sup.2 and/or R.sup.1 and R.sup.6 may represent the necessary atoms to complete a non-aromatic heterocyclic ring,R.sup.7 and R.sup.Type: GrantFiled: September 14, 1981Date of Patent: January 11, 1983Assignee: Minnesota Mining and Manufacturing CompanyInventors: Alan R. Katritzky, Basil J. Graphakos, Girard A. F. Lhommet, Kenneth Reynolds
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Patent number: 4367237Abstract: Prostaglandin analogues of the general formula: ##STR1## [wherein the ring A represents: ##STR2## the ring B represents: ##STR3## (wherein R.sup.6 represents hydrogen, methyl or ethyl, and r is zero, one or two), Y represents ethylene, cis- or trans-vinylene or ethynylene, Z represents a grouping of the formula: --(CH.sub.2).sub.m --, --(CH.sub.2).sub.3 --CHR.sup.7 --, --(CH.sub.2).sub.2 --CHR.sup.7 --CH.sub.2 --, --CH.sub.2 --CHR.sup.7 --(CH.sub.2).sub.2 --, --CHR.sup.7 --(CH.sub.2).sub.3 --, or trans--(CH.sub.2).sub.2 --CH.dbd.CH-- (wherein m is 3, 4 or 5, and R.sup.7 represents methyl or ethyl), R.sup.1 represents a grouping of the formula: --COOR.sup.8, ##STR4## or --CH.sub.2 OR.sup.11 (wherein R.sup.8 represents hydrogen, alkyl, aralkyl, cycloalkyl which is unsubstituted or substituted by at least one alkyl group, or R.sup.Type: GrantFiled: November 27, 1979Date of Patent: January 4, 1983Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Hirohisa Wakatsuka, Katsuichi Shimoji, Sadahiko Iguchi, Yoshitaka Konishi, Hisashi Suga, Yasuyuki Miyata, Yoichi Iguchi, Hajimu Miyake, Masaki Hayashi
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Patent number: 4356186Abstract: Novel acetic acid derivatives of the formula: ##STR1## wherein X is oxygen or sulfur; R.sub.1 is hydrogen or a lower alkyl; R.sub.2 is hydroxy, an alkoxy, an alkenyloxy, a cycloalkyloxy, an aryloxy, a substituted aryloxy, an aryl-lower alkoxy, a substituted aryl-lower alkoxy, an aryl-lower alkenyloxy, a substituted aryl-lower alkenyloxy, an .omega.-disubstituted amino-lower alkoxy, a lower alkoxycrbonyl-lower alkoxy, a lower alkoxy-lower alkoxy, a hydroxy-lower alkoxy-lower alkoxy, an acyl-lower alkoxy, or a group ##STR2## wherein R.sub.3 is hydrogen, hydroxy, a lower alkyl, an aryl-lower alkyl, a hydroxy-lower alkyl, or a carboxy-lower alkyl, R.sub.4 is hydrogen, a lower alkyl or a hydroxy-lower alkyl, or the R.sub.3 and R.sub.4 may combine together with the nitrogen atom to which they are joined to form a heterocyclic group; and the group --CH(R.sub.1)COR.sub.Type: GrantFiled: March 20, 1981Date of Patent: October 26, 1982Assignee: Dainippon Pharmaceutical Co., Ltd.Inventors: Hitoshi Uno, Mikio Kurokawa, Hideo Nakamura
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Patent number: 4344893Abstract: Novel compounds are described which are substituted benzophenone hydrazones. They have pesticidal activity, especially against insects and acarids, and pesticidal compositions and methods are described. Methods of making the compounds, and novel intermediates, are also described.Type: GrantFiled: February 25, 1980Date of Patent: August 17, 1982Assignee: The Boots Company LimitedInventors: Leonard G. Copping, John C. Kerry, Thomas I. Watkins, Robert J. Willis, Bryan H. Palmer
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Patent number: 4335122Abstract: The invention relates to diuretic dihydro-dibenzoxepines-thiepines and -morphanthridones of the formula ##STR1## wherein R is ##STR2## where R.sup.4 is a hydrogen or an alkyl; R.sup.1 is hydrogen or alkyl; R.sup.2 and R.sup.3 are the same or different and are hydrogen, alkyl or R.sup.2 and R.sup.3 are fused to form a pyrrolidino, morpholino, piperidino or azepino ring substituent; Y is hydrogen, halogen and alkoxy, X is ##STR3## where R.sup.4 is as defined above; m is an integer of 0 or 1; and n is an integer of 2 or 3; and the pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: March 18, 1981Date of Patent: June 15, 1982Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Arthur R. McFadden, Daniel E. Aultz
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Patent number: 4329357Abstract: 2,3-Dihydro-1-benzothiepin-4-carboxamides, e.g. those of the formula ##STR1## Am=arylamino or N-alkyl-N-arylamino substituted by R X=HO, alkoxy, alkanoyloxy or alkyleneiminoR=alkyl, alkoxy, alkylmercapto, halo, CF.sub.3, CN, or NO.sub.2n=0-2or their salts with therapeutically useful bases, exhibit anti-inflammatory effects.Type: GrantFiled: February 9, 1981Date of Patent: May 11, 1982Assignee: Ciba-Geigy CorporationInventor: Melvin H. Rosen
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Patent number: 4312868Abstract: Isothiochromans are described. The compounds possess hypotensive and antipsychotic properties; methods and compositions using them are described.Type: GrantFiled: May 15, 1979Date of Patent: January 26, 1982Assignee: The Upjohn CompanyInventor: John M. McCall